3-heterocyclyl-substituted benzoyl derivatives

ABSTRACT

Benzoyl derivatives of the formula I  
                 
where the variables have the following meanings: 
         R 1 , R 2  are hydrogen, nitro, halogen, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl or C 1 -C 6 -haloalkylsulfonyl;    R 3  is hydrogen, halogen or alkyl;    R 4 , R 5  are hydrogen, halogen, cyano, nitro, alkyl, alkoxy, alkylthio, dialkylamino, phenyl or carbonyl, it being possible for the 6 last-mentioned radicals to be substituted;    X is O, S, NR 9 , CO or CR 10 R 11 ;    Y is O, S, NR 12 , CO or CR 13 R 14 ;    R 15  is pyrazole which is unsubstituted or substituted, linked in the 4-position and has attached to it in the 5-position a hydroxyl or sulfonyloxy radical; and the agriculturally useful salts thereof; processes and intermediates for the preparation of the 3-heterocyclyl-substituted benzoyl derivatives; compositions comprising them; and the use of these derivatives or compositions comprising them for controlling undesirable plants.

CROSS-REFERENCE TO RELATED APPLICATIONS

The present application is a 37 C.F.R. § 1.53(b) Divisional of U.S.application Ser. No. 09/748,006 filed Dec. 27, 2000, which in turn is aDivisional of U.S. application Ser. No. 09/091,300 filed Jun. 16, 1998which in turn claims priority of International Application No.PCT/EP98/00069 filed on Jan. 8, 1998. The entire contents of theseapplications are hereby incorporated by reference.

The present invention relates to 3-heterocyclyl-substituted benzoylderivatives of the formula I

-   -   where the variables have the following meanings:    -   R¹, R² are hydrogen, nitro, halogen, cyano, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl or        C₁-C₆-haloalkylsulfonyl;    -   R³ is hydrogen, halogen or C₁-C₆-alkyl;    -   R⁴, R⁵ are hydrogen, halogen, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₄-alkyl, di(C₁-C₄-alkoxy)-C₁-C₄-alkyl,        di(C₁-C₄-alkyl)-amino-C₁-C₄-alkyl,        [2,2-di(C₁-C₄-alkyl)-1-hydrazino]-C₁-C₄-alkyl,        C₁-C₆-alkyliminooxy-C₁-C₄-alkyl,        C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-cyanoalkyl, C₃-C₈-cycloalkyl,        C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₂-C₄-alkoxy, C₁-C₄-haloalkoxy,        hydroxyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkylthio,        C₁-C₄-haloalkylthio, di(C₁-C₄-alkyl)amino, COR⁶, phenyl or        benzyl, it being possible for the two last-mentioned        substituents to be fully or partially halogenated and/or to have        attached to them one to three of the following groups:        -   nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or            C₁-C₄-haloalkoxy;    -   or    -   R⁴ and R⁵ together form a C₂-C₆-alkanediyl chain which can be        mono- to tetrasubstituted by C₁-C₄-alkyl and/or which can be        interrupted by oxygen or by a nitrogen which is unsubstituted or        substituted by C₁-C₄-alkyl;    -   or    -   R⁴ and R⁵ together with the corresponding carbon form a carbonyl        or thiocarbonyl group;    -   R⁶ is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,        C₁-C₄-alkoxy-C₂-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₆-alkenyloxy,        C₃-C₆-alkynyloxy or NR⁷R⁸;    -   R⁷ is hydrogen or C₁-C₄-alkyl;    -   R⁸ is C₁-C₄-alkyl;    -   x is O, S, NR⁹, CO or CR¹⁰OR¹¹;    -   Y is O, S, NR¹², CO or CR¹³R¹⁴;    -   R⁹, R¹² are hydrogen or C₁-C₄-alkyl;    -   R¹⁰, R¹¹, R¹³, R¹⁴ are hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxycarbonyl, C₁-C₄-haloalkoxycarbonyl or CONR⁷R⁸;    -   or    -   R⁴ and R⁹ or R⁴ and R¹⁰ or R⁵ and R¹² or R⁵ and R¹³ together        form a C₂-C₆-alkanediyl chain which can be mono- to        tetrasubstituted by C₁-C₄-alkyl and/or interrupted by oxygen or        by a nitrogen which is unsubstituted or substituted by        C₁-C₄-alkyl;

comprising them for the control of harmful plants.

Pyrazol-4-yl-benzoyl derivatives have been disclosed in the literature,for example in WO 96/26206.

However, the herbicidal properties of the compounds which have beenknown to date and their compatibility properties regarding crop plantsare only moderately satisfactory.

It is an object of the present invention to provide novel, in particularherbicidally active, compounds which have improved properties.

We have found that this object is achieved by the3-hetero-cyclyl-substituted benzoyl derivatives of the formula I and bytheir herbicidal activity.

We have furthermore found herbicidal compositions which comprise thecompounds I and which have a very good herbicidal activity. Moreover, wehave found processes for the preparation of these compositions andmethods of controlling undesirable vegetation using the compounds I.

Depending on the substitution pattern, the compounds of the formula Ican contain one or more chiral centers, in which case they exist asenantiomer or diastereomer mixtures. The present invention relates tothe pure enantiomers or diastereomers and to the mixtures thereof.

The compounds of the formula I may also exist in the form of theiragriculturally useful salts, the type of salt generally being of noimportance. In general, suitable salts are the salts of those cations orthe acid addition salts of those acids whose cations, or anions,respectively, do not adversely affect the herbicidal activity of thecompounds I.

Suitable cations are, in particular, ions of the alkali metals,preferably lithium, sodium and potassium, of the alkaline earth metals,preferably calcium and magnesium, and of the transition metals,preferably manganese, copper, zinc and iron, and also ammonium, it beingpossible in this case, if desired, for one to four hydrogen atoms to bereplaced by C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl, preferably ammonium,dimethylammonium, diisopropylammonium, tetramethylammonium,tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium,di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, in additionphosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfoniumand sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are mainly chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate, and the anions of C₁-C₄-alkanoic acids,preferably formate, acetate, propionate and butyrate.

The organic moieties mentioned for the substituents R¹-R¹⁸ or asradicals on phenyl rings are collective terms for individualenumerations of the individual group members. All hydrocarbon chains,ie. all alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkyliminooxy,alkylcarbonyloxy, alkylthio, haloalkylthio, alkylsulfinyl,haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkoxycarbonyl,haloalkoxycarbonyl, alkenyloxy, alkynyloxy, dialkylamino,dialkylhydrazino, alkoxyalkyl, hydroxyalkoxyalkyl, dialkoxyalkyl,alkylthioalkyl, dialkylaminoalkyl, dialkylhydrazinoalkyl,alkyliminooxyalkyl, alkoxycarbonylalkyl and alkoxyalkoxy moieties, canbe straight-chain or branched. Unless otherwise specified, halogenatedsubstituents preferably have attached to them one to five identical ordifferent halogen atoms. The meaning of halogen is in each casefluorine, chlorine, bromine or iodine.

Other examples of meanings are:

C₁-C₄-alkyl and the alkyl moieties of di-(C₁-C₄-alkoxy)-C₁-C₄-alkyl,[2,2-di(C₁-C₄-alkyl)-1-hydrazino]-C₁-C₄-alkyl,C₁-C₆-alkyliminooxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl andC₁-C₄-alkylcarbonyloxy: for example methyl, ethyl, propyl,1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and1,1-dimethylethyl;

C₁-C₆-alkyl: C₁-C₄-alkyl as mentioned above and, for example, pentyl,1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl and1-ethyl-3-methylpropyl;

C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, for example chloromethyl, dichloromethyl, trichloromethyl,fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl,2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl,2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl,2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyland nonafluorobutyl;

C₁-C₆-haloalkyl: C₁-C₄-haloalkyl as mentioned above and, for example,5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl,undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl,6-iodohexyl and dodecafluorohexyl;

C₁-C₄-cyanoalkyl: for example cyanomethyl, 1-cyanoeth-1-yl,2-cyanoeth-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl,1-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl,3-cyanobut-1-yl, 4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl,1-cyanobut-3-yl, 2-cyanobut-3-yl, 1-cyano-2-methylprop-3-yl,2-cyano-2-methylprop-3-yl, 3-cyano-2-methylprop-3-yl and2-cyanomethylprop-2-yl;

C₁-C₄-alkoxy and the alkoxy moieties of di-(C₁-C₄-alkoxy)-C₁-C₄-alkyland hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl: for example methoxy, ethoxy,propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and1,1-dimethylethoxy;

C₁-C₆-alkoxy: C₁-C₄-alkoxy as mentioned above and, for example, pentoxy,1-methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy, 1,1-dimethylpropoxy,1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy,1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and1-ethyl-2-methylpropoxy;

C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, for example fluoromethoxy, difluoromethoxy, trifluoromethoxy,chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy,2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy,3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy,1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy,4-bromobutoxy and nonafluorobutoxy;

C₁-C₆-haloalkoxy: C₁-C₄-haloalkoxy as mentioned above and, for example,5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy,undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy,6-iodohexoxy and dodecafluorohexoxy;

C₁-C₆-alkyliminooxy and the C₁-C₆-akyliminooxy moieties ofC₁-C₆-alkyliminooxy-C₁-C₄-alkyl: for example methyliminooxy,ethyliminooxy, 1-propyliminooxy, 2-propyliminooxy, 1-butyliminooxy,2-butyliminooxy, 2-methylprop-1-yliminooxy, 1-pentyliminooxy,2-pentyliminooxy, 3-pentyliminooxy, 3-methylbut-2-yliminoxy,2-methylbut-1-yliminooxy, 3-methylbut-1-yliminooxy, 1-hexyliminooxy,2-Hexyliminooxy, 3-hexyliminooxy, 2-methylpent-1-yliminooxy,3-methylpent-1-yliminooxy, 4-methylpent-1-yliminooxy,2-ethylbut-1-yliminooxy, 3-ethylbut-1-yliminooxy,2,3-dimethylbut-1-yliminooxy, 3-methylpent-2-yliminooxy,4-methylpent-2-yliminooxy and 3,3-dimethylbut-2-yliminooxy;

C₁-C₄-alkylthio: for example methylthio, ethylthio, propylthio,1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and1,1-dimethylethylthio;

C₁-C₆-alkylthio: C₁-C₄-alkylthio as mentioned above and, for example,pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio,2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio,2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio,1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio,1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and1-ethyl-2-methylpropylthio;

C₁-C₄-haloalkylthio: a C₁-C₄-alkylthio radical as mentioned above, whichis partially or fully substituted by fluorine, chlorine, bromine and/oriodine, for example fluoromethylthio, difluoromethylthio,trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio,2-fluorethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio,2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio,2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio,pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio,2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio,3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,2,3-dichloropropylthio, 3,3,3-trifluoropropylthio,3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio,heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio,1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio,4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio andnonafluorobutylthio;

C₁-C₆-haloalkylthio: C₁-C₄-haloalkylthio as mentioned above and, forexample, 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio,5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio,6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio anddodecafluorohexylthio;

C₁-C₆-alkylsulfinyl(C₁-C₆-alkyl-S(═O)—): for example methylsulfinyl,ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl,1-methylpropylsulfinyl, 2-methylpropylsulfinyl,1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl,2-methylbutylsulfinyl, 3-methylbutylsulfinyl,2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl,1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl,1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl,4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl,1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl,2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl,3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl;

C₁-C₆-haloalkylsulfinyl: a C₁-C₆-alkylsulfinyl radical as mentionedabove which is partially or fully substituted by fluorine, chlorine,bromine and/or iodine, for example fluoromethylsulfinyl,difluoromethylsulfinyl, trifluoromethylsulfinyl,chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl,2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl,2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl,2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl,2-chloro-2-fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl,2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl,2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl,3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl,2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl,3,3,3-trichloropropylsulfinyl, 2,2,3,3,3-pentafluoropropylsulfinyl,heptafluoropropylsulfinyl, 1-(fluoromethyl)-2-fluoroethylsulfinyl,1-(chloromethyl)-2-chloroethylsulfinyl,1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl,4-chlorobutylsulfinyl, 4-bromobutylsulfinyl, nonafluorobutylsulfinyl,5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopentylsulfinyl,5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl,6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl anddodecafluorohexylsulfinyl;

C₁-C₆-alkylsulfonyl(C₁-C₆-alkyl-S(═O)₂—): for example methylsulfonyl,ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl,1-methylpropylsulfonyl, 2-methylpropylsulfonyl,1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl,2-methylbutylsulfonyl, 3-methylbutylsulfonyl,1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl,2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl,1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl,4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl;

C₁-C₆-haloalkylsulfonyl: a C₁-C₆-alkylsulfonyl radical as mentionedabove which is partially or fully substituted by fluorine, chlorine,bromine and/or iodine, for example fluoromethylsulfonyl,difluoromethylsulfonyl, trifluoromethylsulfonyl,chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl,2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl,2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl,2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl,2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl,2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl,2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl,3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl,2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl,heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl,1-(chloromethyl)-2-chloroethylsulfonyl,1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,4-chlorobutylsulfonyl, 4-bromobutylsulfonyl, nonafluorobutylsulfonyl,5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl,5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl,6-iodohexylsulfonyl and dodecafluorohexylsulfonyl;

C₁-C₄-alkoxycarbonyl: for example methoxycarbonyl, ethoxycarbonyl,propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl,1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl and1,1-dimethoxycarbonyl;

C₁-C₄-haloalkoxycarbonyl: a C₁-C₄-alkoxycarbonyl as mentioned abovewhich is partially or fully substituted by fluorine, chlorine, bromineand/or iodine, for example fluoromethoxycarbonyl,difluoromethoxycarbonyl, trifluoromethoxycarbonyl,chlorodifluoromethoxycarbonyl, bromodifluoromethoxycarbonyl,2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl,2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl,2,2,2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl,2-chloro-2,2-difluoroethoxycarbonyl,2,2-dichloro-2-fluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl,pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl,3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl,3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl,2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl,2,3-dichloropropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl,3,3,3-trichloropropoxycarbonyl, 2,2,3,3,3-pentafluoropropoxycarbonyl,heptafluoropropoxycarbonyl, 1-(fluoromethyl)-2-fluoroethoxycarbonyl,1-(chloromethyl)-2-chloroethoxycarbonyl,1-(bromomethyl)-2-bromoethoxycarbonyl, 4-fluorobutoxycarbonyl,4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl and 4-iodobutoxycarbonyl;

C₃-C₆-alkenyloxy: for example prop-1-en-1-yloxy, prop-2-en-1-yloxy,1-methylethenyloxy, buten-1-yloxy, buten-2-yloxy, buten-3-yloxy,1-methylprop-1-en-1-yloxy, 2-methylprop-1-en-1-yloxy,1-methylprop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, penten-1-yloxy,penten-2-yloxy, penten-3-yloxy, penten-4-yloxy,1-methylbut-1-en-1-yloxy, 2-methylbut-1-en-1-yloxy,3-methylbut-1-en-1-yloxy, 1-methylbut-2-en-1-yloxy,2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yloxy,1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy,3-methylbut-3-en-1-yloxy, 1,1-dimethylprop-2-en-1-yloxy,1,2-dimethylprop-1-en-1-yloxy, 1,2-dimethylprop-2-en-1-yloxy,1-ethylprop-1-en-2-yloxy, 1-ethylprop-2-en-1-yloxy, hex-1-en-1-yloxy,hex-2-en-1-yloxy, hex-3-en-1-yloxy, hex-4-en-1-yloxy, hex-5-en-1-yloxy,1-methylpent-1-en-1-yloxy, 2-methylpent-1-en-1-yloxy,3-methylpent-1-en-1-yloxy, 4-methylpent-1-en-1-yloxy,1-methylpent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy,3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy,1-methylpent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy,3-methylpent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy,1-methylpent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy,3-methylpent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy,1,1-dimethylbut-2-en-1-yloxy, 1,1-dimethylbut-3-en-1-yloxy,1,2-dimethylbut-1-en-1-yloxy, 1,2-dimethylbut-2-en-1-yloxy,1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-1-en-1-yloxy,1,3-dimethylbut-2-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy,2,2-dimethylbut-3-en-1-yloxy, 2,3-dimethylbut-1-en-1-yloxy,2,3-dimethylbut-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy,3,3-dimethylbut-1-en-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy,1-ethylbut-1-en-1-yloxy, 1-ethylbut-2-en-1-yloxy,1-ethylbut-3-en-1-yloxy, 2-ethylbut-1-en-1-yloxy,2-ethylbut-2-en-1-yloxy, 2-ethylbut-3-en-1-yloxy,1,1,2-trimethylprop-2-en-1-yloxy, 1-ethyl-1-methylprop-2-en-1-yloxy,1-ethyl-2-methylprop-1-en-1-yloxy and 1-ethyl-2-methylprop-2-en-1-yloxy;

C₃-C₆-alkynyloxy: for example prop-1-yn-1-yloxy, prop-2-yn-1-yloxy,but-1-yn-1-yloxy, but-1-yn-3-yloxy, but-1-yn-4-yloxy, but-2-yn-1-yloxy,pent-1-yn-1-yloxy, pent-1-yn-3-yloxy, pent-1-yn-4-yloxy,pent-1-yn-5-yloxy, pent-2-yn-1-yloxy, pent-2-yn-4-yloxy,pent-2-yn-5-yloxy, 3-methylbut-1-yn-3-yloxy, 3-methylbut-1-yn-4-yloxy,hex-1-yn-1-yloxy, hex-1-yn-3-yloxy, hex-1-yn-4-yloxy, hex-1-yn-5-yloxy,hex-1-yn-6-yloxy, hex-2-yn-1-yloxy, hex-2-yn-4-yloxy, hex-2-yn-5-yloxy,hex-2-yn-6-yloxy, hex-3-yn-1-yloxy, hex-3-yn-2-yloxy,3-methylpent-1-yn-1-yloxy, 3-methylpent-1-yn-3-yloxy,3-methylpent-1-yn-4-yloxy, 3-methylpent-1-yn-5-yloxy,4-methylpent-1-yn-1-yloxy, 4-methylpent-2-yn-4-yloxy and4-methylpent-2-yn-5-yloxy;

di(C₁-C₄-alkyl)amino: for example N,N-dimethylamino, N,N-diethylamino,N,N-dipropylamino, N,N-di(1-methylethyl)amino, N,N-dibutylamino,N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino,N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino,N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino,N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino,N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino,N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino,N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino,N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino,N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino,N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino,N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino,N-(1-methylethyl)-N-(1-methylpropyl)amino,N-(1-methylethyl)-N-(2-methylpropyl)amino,N-(1,1-dimethylethyl)-N-(1-methylethyl)amino,N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino,N-butyl-N-(1,1-dimethylethyl)amino,N-(1-methylpropyl)-N-(2-methylpropyl)amino,N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino andN-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;

[2,2-di(C₁-C₄-alkyl)-1-hydrazino], and the dialkylhydrazino moieties of(2,2-di(C₁-C₄-alkyl)-1-hydrazino]-C₁-C₄-alkyl: for example2,2-dimethylhydrazino-1,2,2-diethylhydrazino-1,2,2-dipropylhydrazino-1,2,2-di(1-methylethyl)-1-hydrazino,2,2-dibutylhydrazino-1,2,2-di(1-methylpropyl)-1-hydrazino,2,2-di(2-methylpropyl)-1-hydrazino,2,2-di(1,1-dimethylethyl)-1-hydrazino, 2-ethyl-2-methyl-1-hydrazino,2-methyl-2-propyl-1-hydrazino, 2-methyl-2-(1-methylethyl)-1-hydrazino,2-butyl-2-methyl-1-hydrazino, 2-methyl-2-(1-methylpropyl)-1-hydrazino,2-methyl-2-(2-methylpropyl)-1-hydrazino,2-(1,1-dimethylethyl)-2-methyl-1-hydrazino,2-ethyl-2-propyl-1-hydrazino, 2-ethyl-2-(1-methylethyl)-1-hydrazino,2-butyl-2-ethyl-1-hydrazino, 2-ethyl-2-(1-methylpropyl)-1-hydrazino,2-ethyl-2-(2-methylpropyl)-1-hydrazino,2-ethyl-2-(1,1-dimethylethyl)-1-hydrazino,2-(1-methylethyl)-2-propyl-1-hydrazino, 2-butyl-2-propyl-1-hydrazino,2-(1-methylpropyl)-2-propyl-1-hydrazino,2-(2-methylpropyl)-2-propyl-1-hydrazino,2-(1,1-dimethylethyl)-2-propyl-1-hydrazino,2-butyl-2-(1-methylethyl)-1-hydrazino,2-(1-methylethyl)-2-(1-methylpropyl)-1-hydrazino,2-(1-methylethyl)-2-(2-methylpropyl)-1-hydrazino,2-(1,1-dimethylethyl)-2-(1-methylethyl)-1-hydrazino,2-butyl-2-(1-methylpropyl)-1-hydrazino,2-butyl-2-(2-methylpropyl)-1-hydrazino,2-butyl-2-(1,1-dimethylethyl)-1-hydrazino,2-(1-methylpropyl)-2-(2-methylpropyl)-1-hydrazino,2-(1,1-dimethylethyl)-2-(1-methylpropyl)-1-hydrazino and2-(1,1-dimethylethyl)-2-(2-methylpropyl)-1-hydrazino;

di(C₁-C₄-alkyl)amino-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted bydi(C₁-C₄-alkyl)amino as mentioned above, for exampleN,N-dimethylaminomethyl, N,N-diethylaminomethyl,N,N-dipropylaminomethyl, N,N-di(1-methylethyl)aminomethyl,N,N-dibutylaminomethyl, N,N-di(1-methylpropyl)aminomethyl,N,N-di(2-methylpropyl)aminomethyl, N,N-di(1,1-dimethylethyl)aminomethyl,N-ethyl-N-methylaminomethyl, N-methyl-N-propylaminomethyl,N-methyl-N-(1-methylethyl)aminomethyl, N-butyl-N-methylaminomethyl,N-methyl-N-(1-methylpropyl)aminomethyl,N-methyl-N-(2-methylpropyl)aminomethyl,N-(1,1-dimethylethyl)-N-methylaminomethyl, N-ethyl-N-propylaminomethyl,N-ethyl-N-(1-methylethyl)aminomethyl, N-butyl-N-ethylaminomethyl,N-ethyl-N-(1-methylpropyl)aminomethyl,N-ethyl-N-(2-methylpropyl)aminomethyl,N-ethyl-N-(1,1-di-methylethyl)aminomethyl,N-(1-methylethyl)-N-propylaminomethyl, N-butyl-N-propylaminomethyl,N-(1-methylpropyl)-N-propylaminomethyl,N-(2-methylpropyl)-N-propylaminomethyl,N-(1,1-dimethylethyl)-N-propylaminomethyl,N-butyl-N-(1-methylethyl)aminomethyl,N-(1-methylethyl)-N-(1-methylpropyl)aminomethyl,N-(1-methylethyl)-N-(2-methylpropyl)aminomethyl,N-(1,1-dimethylethyl)-N-(1-methylethyl)aminomethyl,N-butyl-N-(1-methylpropyl)aminomethyl,N-butyl-N-(2-methylpropyl)aminomethyl,N-butyl-N-(1,1-dimethylethyl)aminomethyl,N-(1-methylpropyl)-N-(2-methylpropyl)aminomethyl,N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminomethyl,N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminomethyl,2-(N,N-dimethylamino)ethyl, 2-(N,N-diethylamino)ethyl,2-(N,N-dipropylamino)ethyl, 2-[N,N-di(1-methylethyl)amino]ethyl,2-[N,N-dibutylamino]ethyl, 2-[N,N-di(1-methylpropyl)amino]ethyl,2-[N,N-di(2-methylpropyl)amino]ethyl,2-[N,N-di(1,1-dimethylethyl)amino]ethyl, 2-[N-ethyl-N-methylamino]ethyl,2-[N-methyl-N-propylamino]ethyl,2-[N-methyl-N-(1-methylethyl)amino]ethyl,2-[N-butyl-N-methylamino]ethyl,2-[N-methyl-N-(1-methylpropyl)amino]ethyl,2-[N-methyl-N-(2-methylpropyl)amino]ethyl,2-[N-(1,1-dimethylethyl)-N-methylamino]ethyl,2-[N-ethyl-N-propylamino]ethyl, 2-[N-ethyl-N-(1-methylethyl)amino]ethyl,2-[N-butyl-N-ethylamino]ethyl, 2-[N-ethyl-N-(1-methylpropyl)amino]ethyl,2-[N-ethyl-N-(2-methylpropyl)amino]ethyl,2-[N-ethyl-N-(1,1-dimethylethylamino]ethyl,2-[N-(1-methylethyl)-N-propylamino]ethyl,2-[N-butyl-N-propylamino]ethyl,2-[N-(1-methylpropyl)-N-propylamino]ethyl,2-[N-(2-methylpropyl)-N-propylamino]ethyl,2-[N-(1,1-dimethylethyl)-N-propylamino]ethyl,2-[N-butyl-N-(1-methylethyl)amino]ethyl,2-[N-(1-methylethyl)-N-(1-methylpropyl)amino]ethyl,2-[N-(1-methylethyl)-N-(2-methylpropyl)amino]ethyl,2-[N-(1,1-dimethylethyl)-N-(1-methylethyl)amino]ethyl,2-[N-butyl-N-(1-methylpropyl)amino]ethyl,2-[N-butyl-N-(2-methylpropyl)amino]ethyl,2-[N-butyl-N-(1,1-dimethylethyl)amino]ethyl,2-[N-(1-methylpropyl)-N-(2-methylpropyl)amino]ethyl,2-[N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino]ethyl,2-[N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino]ethyl,3-(N,N-dimethylamino)propyl, 3-(N,N-diethylamino)propyl,4-(N,N-dimethylamino)butyl und 4-(N,N-diethylamino)butyl;

C₁-C₄-alkoxy-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted byC₁-C₄-alkoxy as mentioned above, for example methoxymethyl,ethoxymethyl, propoxymethyl, (1-methylethoxy)methyl, butoxymethyl,(1-methylpropoxy)methyl, (2-methylpropoxy)methyl,(1,1-dimethylethoxy)methyl, 2-(methoxy)ethyl, 2-(ethoxy)ethyl,2-(propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl,2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl,2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)-propyl, 2-(ethoxy)propyl,2-(propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(butoxy)propyl,2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl,2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)-propyl,3-(propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(butoxy)propyl,3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,2-(propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(butoxy)butyl,2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl,3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl,4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl and4-(1,1-dimethylethoxy)butyl;

C₁-C₄-alkylthio-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted byC₁-C₄-alkylthio as mentioned above, for example methylthiomethyl,ethylthiomethyl, propylthiomethyl, (1-methylethylthio)methyl,butylthiomethyl, (1-methylpropylthio)methyl, (2-methylpropylthio)methyl,(1,1-dimethylethylthio)methyl, 2-methylthioethyl, 2-ethylthioethyl,2-(propylthio)ethyl, 2-(1-methylethylthio)ethyl, 2-(butylthio)ethyl,2-(1-methylpropylthio)ethyl, 2-(2-methylpropylthio)ethyl,2-(1,1-dimethylethylthio)ethyl, 2-(methylthio)propyl,3-(methylthio)propyl, 2-(ethylthio)propyl, 3-(ethylthio)propyl,3-(propylthio)propyl, 3-(butylthio)propyl, 4-(methylthio)butyl,4-(ethylthio)butyl, 4-(propylthio)butyl and 4-(butylthio)butyl;

C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl: C₁-C₄-alkyl which is substituted byC₁-C₄-alkoxycarbonyl as mentioned above, for examplemethoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl,(1-methylethoxycarbonyl)methyl, butoxycarbonylmethyl,(1-methylpropoxycarbonyl)methyl, (2-methylpropoxycarbonyl)methyl,(1,1-dimethylethoxycarbonyl)methyl, 2-(methoxycarbonyl)ethyl,2-(ethoxycarbonyl)ethyl, 2-(propoxycarbonyl)ethyl,2-(1-methylethoxycarbonyl)ethyl, 2-(butoxycarbonyl)ethyl,2-(1-methylpropoxycarbonyl)ethyl, 2-(2-methylpropoxycarbonyl)ethyl,2-(1,1-dimethylethoxycarbonyl)ethyl, 2-(methoxycarbonyl)propyl,2-(ethoxycarbonyl)propyl, 2-(propoxycarbonyl)propyl,2-(1-methylethoxycarbonyl)propyl, 2-(butoxycarbonyl)propyl,2-(1-methylpropoxycarbonyl)propyl, 2-(2-methylpropoxycarbonyl)propyl,2-(1,1-dimethylethoxycarbonyl)propyl, 3-(methoxycarbonyl)propyl,3-(ethoxycarbonyl)propyl, 3-(propoxycarbonyl)propyl,3-(1-methylethoxycarbonyl)propyl, 3-(butoxycarbonyl)propyl,3-(1-methylpropoxycarbonyl)propyl, 3-(2-methylpropoxycarbonyl)propyl,3-(1,1-dimethylethoxycarbonyl)propyl, 2-(methoxycarbonyl)butyl,2-(ethoxycarbonyl)butyl, 2-(propoxycarbonyl)butyl,2-(1-methylethoxycarbonyl)butyl, 2-(butoxycarbonyl)butyl,2-(1-methylpropoxycarbonyl)butyl, 2-(2-methylpropoxycarbonyl)butyl,2-(1,1-dimethylethoxycarbonyl)butyl, 3-(methoxycarbonyl)butyl,3-(ethoxycarbonyl)butyl, 3-(propoxycarbonyl)butyl,3-(1-methylethoxycarbonyl)butyl, 3-(butoxycarbonyl)butyl,3-(1-methylpropoxycarbonyl)butyl, 3-(2-methylpropoxycarbonyl)butyl,3-(1,1-dimethylethoxycarbonyl)butyl, 4-(methoxycarbonyl)-butyl,4-(ethoxycarbonyl)butyl, 4-(propoxycarbonyl)butyl,4-(1-methylethoxycarbonyl)butyl, 4-(butoxycarbonyl)butyl,4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy und4-(1,1-dimethylethoxycarbonyl)butyl;

C₁-C₄-alkoxy-C₂-C₄-alkoxy: C₂-C₄-alkoxy which is substituted byC₁-C₄-alkoxy as mentioned above, for example 2-(methoxy)ethoxy,2-(ethoxy)ethoxy, 2-(propoxy)ethoxy, 2-(1-methylethoxy)ethoxy,2-(butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy,2-(1,1-dimethylethoxy)ethoxy, 2-(methoxy)propoxy, 2-(ethoxy)propoxy,2-(propoxy)propoxy, 2-(1-methylethoxy)propoxy, 2-(butoxy)propoxy,2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy,2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy, 3-(ethoxy)propoxy,3-(propoxy)propoxy, 3-(1-methylethoxy)propoxy, 3-(butoxy)propoxy,3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy,3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy, 2-(ethoxy)butoxy,2-(propoxy)butoxy, 2-(1-methylethoxy)butoxy, 2-(butoxy)butoxy,2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy,2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy, 3-(ethoxy)-butoxy,3-(propoxy)butoxy, 3-(1-methylethoxy)butoxy, 3-(butoxy)butoxy,3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy,3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy, 4-(ethoxy)butoxy,4-(propoxy)butoxy, 4-(1-methylethoxy)butoxy, 4-(butoxy)butoxy,4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy and4-(1,1-dimethylethoxy)butoxy;

C₂-C₆-alkanediyl: for example ethane-1,2-diyl, propane-1,3-diyl,butane-1,4-diyl, pentane-1,5-diyl and hexane-1,6-diyl;

C₃-C₈-cycloalkyl: for example cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl or cyclooctyl;

All phenyl rings are preferably unsubstituted or have attached to themone to three halogen atoms and/or a nitro group, a cyano radical and/orone or two methyl, trifluoromethyl, methoxy or trifluoromethoxysubstituents.

Preference is given to the 3-heterocyclyl-substituted benzoylderivatives of the formula I where the variables have the followingmeanings:

-   -   R¹, R² are hydrogen, nitro, halogen, cyano, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl or        C₁-C₆-haloalkylsulfonyl;    -   R³ is hydrogen, halogen or C₁-C₆-alkyl;    -   R⁴, R⁵ are hydrogen, halogen, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₄-alkyl, di(C₁-C₄-alkoxy)-C₁-C₄-alkyl,        di(C₁-C₄-alkyl)-amino-C₁-C₄-alkyl,        [2,2-di(C₁-C₄-alkyl)-1-hydrazino]-C₁-C₄-alkyl,        C₁-C₆-alkyliminooxy-C₁-C₄-alkyl,        C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-cyanoalkyl, C₃-C₈-cycloalkyl,        C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₂-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, di(C₁-C₄-alkyl)amino,        COR⁶, phenyl or benzyl, it being possible for the two        last-mentioned substituents to be fully or partially halogenated        and/or to have attached to them one to three of the following        groups:        -   nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or            C₁-C₄-haloalkoxy;    -   or    -   R⁴ and R⁵ together form a C₂-C₆-alkanediyl chain which can be        mono- to tetrasubstituted by C₁-C₄-alkyl and/or which can be        interrupted by oxygen or by a nitrogen which is unsubstituted or        substituted [lacuna] C₁-C₄-alkyl;    -   or    -   R⁴ and R⁵ together with the corresponding carbon form a carbonyl        or thiocarbonyl group;    -   R⁶ is C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,        C₁-C₄-alkoxy-C₂-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₆-alkenyloxy,        C₃-C₆-alkynyloxy or NR⁷R⁸;    -   R⁷ is hydrogen or C₁-C₄-alkyl;    -   R⁸ is C₁-C₄-alkyl;    -   X is O, S, NR⁹, CO or CR¹⁰R¹¹;    -   Y is O, S, NR¹², CO or CR¹³R¹⁴;    -   R⁹, R¹² are hydrogen or C₁-C₄-alkyl;    -   R¹⁰, R¹¹, R¹³, R¹⁴ are hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxycarbonyl, C₁-C₄-haloalkoxycarbonyl or CONR⁷R⁸;    -   or    -   R⁴ and R⁹ or R⁴ and R¹⁰ or R⁵ and R¹² or R⁵ and R¹³ together        form a C₂-C₆-alkanediyl chain which can be mono- to        tetrasubstituted by C₁-C₄-alkyl and/or interrupted by oxygen or        by a nitrogen which is unsubstituted or substituted by        C₁-C₄-alkyl;    -   R¹⁵ is a pyrazole of the formula II which is linked in the        4-position    -   where    -   R¹⁶ is C₁-C₆-alkyl;    -   Z is H or SO₂R¹⁷;    -   R¹⁷ is C₁-C₄-alkyl, C₁-C₄-haloalkyl, phenyl or phenyl which is        partially or fully halogenated and/or has attached to it one to        three of the following groups:    -   nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or        C₁-C₄-haloalkoxy;    -   R¹⁸ is hydrogen or C₁-C₆-alkyl;    -   where X and Y are not simultaneously oxygen or sulfur;

with the exception of4-[2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-ethyl-5-hydroxy-1H-pyrazole,4-[2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-benzoyl]-1,3-dimethyl-5-hydroxy-1H-pyrazole,4-[2-chloro-3-(5-cyano-4,5-dihydroisoxazol-3-yl)-4-methyl-sulfonylbenzoyl]-1,3-dimethyl-5-hydroxy-1H-pyrazole,4-[2-chloro-3-(4,5-dihydrothiazol-2-yl)-4-methylsulfonylbenzoyl]-1,3-dimethyl-5-hydroxy-1H-pyrazoleand4-[2-chloro-3-(thiazoline-4,5-dion-2-yl)-4-methylsulfonyl-benzoyl]-1,3-dimethyl-5-hydroxy-1H-pyrazole;

or the agriculturally useful salts thereof.

With a view to the use of the compounds of the formula I according tothe invention as herbicides, the variables preferably have the followingmeanings, in each case alone or in combination:

-   -   R¹, R² are nitro, halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio,        C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl or        C₁-C₆-haloalkylsulfonyl;        -   especially preferably nitro, halogen such as, for example,            chlorine and bromine, C₁-C₆-alkyl such as, for example,            methyl and ethyl, C₁-C₆-alkoxy such as, for example, methoxy            and ethoxy, C₁-C₆-haloalkyl such as, for example,            difluoromethyl and trifluoromethyl, C₁-C₆-alkylthio such as,            for example, methylthio and ethylthio, C₁-C₆-alkylsulfinyl            such as, for example, methylsulfinyl and ethylsulfinyl,            C₁-C₆-alkylsulfonyl such as, for example, methylsulfonyl,            ethylsulfonyl and propylsulfonyl or C₁-C₆-haloalkylsulfonyl            such as, for example, trifluoromethylsulfonyl and            pentafluoroethylsulfonyl;    -   R³ is hydrogen;    -   R⁴, R⁵ are hydrogen, halogen, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₄-alkyl, di(C₁-C₄-alkoxy)-C₁-C₄-alkyl,        di(C₁-C₄-alkyl)amino-C₁-C₄-alkyl,        [2,2-di(C₁-C₄-alkyl)hydrazino-1]-C₁-C₄-alkyl,        C₁-C₆-alkyliminooxy-C₁-C₄-alkyl,        C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-cyanoalkyl, C₃-C₈-cycloalkyl,        C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₂-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, di(C₁-C₄-alkyl)amino,        COR⁶, phenyl or benzyl, it being possible for the two        last-mentioned substituents to be partially or fully halogenated        and/or to have attached to them one to three of the following        groups:        -   nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or            C₁-C₄-haloalkoxy;    -   or    -   R⁴ and R⁵ together form a C₂-C₆-alkanediyl chain which can be        mono- to tetrasubstituted by C₁-C₄-alkyl and/or which can be        interrupted by oxygen or by a nitrogen which is unsubstituted or        substituted by C₁-C₄-alkyl;        -   R⁴ is especially preferably hydrogen, C₁-C₄-alkyl,            C₁-C₄-haloalkyl, C₁-C₄-alkoxycarbonyl or CONR⁷R⁸;        -   R⁵ is especially preferably hydrogen or C₁-C₄-alkyl; or        -   R⁴ and R⁵ especially preferably form a C₂-C₆-alkanediyl            chain which can be mono- to tetrasubstituted by C₁-C₄-alkyl            and/or which can be interrupted by oxygen or by a nitrogen            which is unsubstituted or substituted by C₁-C₄-alkyl;    -   R⁶ is C₁-C₄-alkyl, C₁-C₄-alkoxy or NR⁷R⁸;    -   R⁷ is hydrogen or C₁-C₄-alkyl;    -   R⁸ is C₁-C₄-alkyl;    -   X is O, S, NR⁹, CO or CR¹⁰R¹¹;    -   Y is O, S, NR¹² or CR¹³R¹⁴;    -   R⁹, R¹² are hydrogen or C₁-C₄-alkyl;    -   R¹⁰, R¹¹, R¹³, R¹⁴ are hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxycarbonyl, C₁-C₄-haloalkoxycarbonyl or CONR⁷R⁸;    -   or    -   R⁴ and R⁹ or R⁴ and R¹⁰ or R⁵ and R¹² or R⁵ and R¹³ together        form a C₂-C₆-alkanediyl chain which can be mono- to        tetrasubstituted by C₁-C₄-alkyl and/or which can be interrupted        by oxygen or by a nitrogen which is unsubstituted or substituted        by C₁-C₄-alkyl;    -   R¹⁶ is C₁-C₆-alkyl;        -   especially preferably methyl, ethyl, propyl, 2-methylpropyl            or butyl;    -   Z is H or SO₂R¹⁷;    -   R¹⁷ is C₁-C₄-alkyl, phenyl or phenyl which is partially or fully        halogenated and/or has attached to it one to three of the        following groups:        -   nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or            C₁-C₄-haloalkoxy;    -   R¹⁸ is hydrogen or C₁-C₆-alkyl;        -   especially preferably hydrogen or methyl.

The following embodiments of the 3-heterocyclyl-substituted benzoylderivatives of the formula I must be emphasized:

-   1. In a preferred embodiment of the 3-heterocyclyl-substituted    benzoyl derivatives of the formula I, Z is SO₂R¹⁷.    -   Especially preferred are the 3-heterocyclyl-substituted benzoyl        derivatives of the formula I, where R¹⁸ is hydrogen.    -   Also especially preferred are 3-heterocyclyl-substituted benzoyl        derivatives of the formula I, where R¹⁸ is methyl.        -   Particularly preferred are 3-heterocylyl-substituted benzoyl            derivatives of the formula I, where R¹⁷ is C₁-C₄-alkyl.-   2. In a further preferred embodiment of the    3-heterocyclyl-substituted benzoyl derivatives of the formula I, Z    is hydrogen.    -   Especially preferred are 3-heterocyclyl-substituted benzoyl        derivatives of the formula I where X is oxygen and Y is CR¹³R¹⁴.        -   Particularly preferred are 3-heterocyclyl-substituted            benzoyl derivatives of the formula I where            -   R⁴ is halogen, nitro, C₁-C₄-alkyl,                C₁-C₄-alkoxy-C₁-C₄-alkyl,                C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,                C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-haloalkyl,                C₁-C₄-cyanoalkyl, C₃-C₈-cycloalkyl, C₁-C₄-alkoxy,                C₁-C₄-Alkoxy-C₂-C₄-alkoxy, C₁-C₄-haloalkoxy,                C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,                di(C₁-C₄-alkyl)amino, COR⁶, phenyl or benzyl, it being                possible for the two last-mentioned substituents to be                partially or fully halogenated and/or to have attached                to them one to three of the following groups:                -   nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,                    C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;            -   R⁵ is hydrogen or C₁-C₄-alkyl;            -   or            -   R⁴ and R⁵ together form a C₂-C₆-alkanediyl chain which                can be mono- to tetrasubstituted by C₁-C₄-alkyl and/or                which can be interrupted by oxygen or by a nitrogen                which is unsubstituted or substituted by C₁-C₄-alkyl;            -   or            -   R⁵ and R¹³ together form a C₂-C₆-alkanediyl chain which                can be mono- to tetrasubstituted by C₁-C₄-alkyl and/or                which can be interrupted by oxygen or by a nitrogen                which is unsubstituted or substituted by C₁-C₄-alkyl.            -   Extraordinarily preferred are 3-heterocyclyl-substituted                benzoyl derivatives of the formula I where            -   R⁴ is C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxycarbonyl                or CONR⁷R⁸;            -   R⁵ is hydrogen or C₁-C₄-alkyl;            -   or            -   R⁴ and R⁵ together form a C₂-C₆-alkanediyl chain which                can be mono- to tetrasubstituted by C₁-C₄-alkyl and/or                which can be interrupted by oxygen or by a nitrogen                which is unsubstituted or substituted by C₁-C₄-alkyl;            -   or            -   R⁵ and R¹³ together form a C₂-C₆-alkanediyl chain which                can be mono- to tetrasubstituted by C₁-C₄-alkyl and/or                which can be interrupted by oxygen or by a nitrogen                which is unsubstituted or substituted by C₁-C₄-alkyl.            -   Especially extraordinarily preferred are                3-heterocyclyl-substituted benzoyl derivatives of the                formula I where R¹⁸ is hydrogen.        -   Also particularly preferred are 3-heterocyclyl-substituted            benzoyl derivatives of the formula I where R⁴ and R⁵ are            hydrogen.            -   Extraordinarily preferred are 3-heterocyclyl-substituted                benzoyl derivatives of the formula I where R¹⁸ is                hydrogen.                -   Especially extraordinarily preferred are                    3-heterocyclyl-substituted benzoyl derivatives of                    the formula I where                -   R¹ is nitro, C₁-C₆-alkyl such as, for example,                    methyl and ethyl, C₁-C₆-alkoxy such as, for example,                    methoxy and ethoxy, C₁-C₆-haloalkyl such as, for                    example, difluoromethyl and trifluoromethyl,                    C₁-C₆-alkylsulfonyl such as, for example,                    methylsulfonyl, ethylsulfonyl and propylsulfonyl, or                    C₁-C₆-haloalkylsulfonyl such as, for example,                    trifluoromethylsulfonyl and                    pentafluoroethylsulfonyl;                -   Also especially extraordinarily preferred are                    3-heterocyclyl-substituted benzoyl derivatives of                    the formula I where                -   R² is nitro, halogen such as, for example, chlorine                    and bromine, C₁-C₆-alkyl such as, for example,                    methyl and ethyl, C₁-C₆-haloalkyl such as, for                    example, difluoromethyl and trifluoromethyl,                    C₁-C₆-alkylthio such as, for example, methylthio and                    ethylthio, C₁-C₆-alkylsulfinyl such as, for example,                    methylsulfinyl and ethylsulfinyl,                    C₁-C₆-alkylsulfonyl such as, for example,                    methylsulfonyl, ethylsulfonyl and propylsulfonyl, or                    C₁-C₆-haloalkylsulfonyl such as, for example,                    trifluomethylsulfonyl and pentafluoroethylsulfonyl.                -   Also especially extraordinarily preferred is                    4-[2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-methyl-5-hydroxy-1H-pyrazole.                -   Also especially extraordinarily preferred are the                    agriculturally useful salts of                    4-[2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-benzoyl]-1-methyl-5-hydroxy-1H-pyrazole,                    in particular the alkali metal salts, such as, for                    example, lithium, sodium and potassium, and the                    ammonium salts, it being possible in this case, if                    desired, for one to four hydrogen atoms to be                    replaced by C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl,                    C₁-C₄-alkoxy-C₁-C₄-alkyl,                    hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl,                    preferably ammonium, dimethylammonium,                    diisopropylammonium, tetramethylammonium,                    tetrabutylammonium,                    2-(2-hydroxyeth-1-oxy)eth-1-ylammonium,                    di(2-hydroxyeth-1-yl)ammonium,                    trimethylbenzylammonium.                -   Also extraordinarily preferred are                    3-heterocyclyl-substituted benzoyl derivatives of                    the formula I where R¹⁸ is methyl.                -   Especially extraordinarily preferred are                    3-heterocyclyl-substituted benzoyl derivatives of                    the formula I where                -   R¹ is nitro, C₁-C₆-alkyl such as, for example,                    methyl and ethyl, C₁-C₆-alkoxy such as, for example,                    methoxy and ethoxy, C₁-C₆-haloalkyl such as, for                    example, difluoromethyl and trifluoromethyl,                    C₁-C₆-alkylsulfonyl such as, for example,                    methylsulfonyl, ethylsulfonyl and propylsulfonyl, or                    C₁-C₆-haloalkylsulfonyl, for example                    trifluoromethylsulfonyl and                    pentafluoroethylsulfonyl.                -   Also especially extraordinarily preferred are                    3-heterocyclyl-substituted benzoyl derivatives of                    the formula I where                -   R² is nitro, halogen such as, for example, chlorine                    and bromine, C₁-C₆-alkyl such as, for example,                    methyl and ethyl, C₁-C₆-haloalkyl such as, for                    example, difluoromethyl and trifluoromethyl,                    C₁-C₆-alkylthio such as, for example, methylthio and                    ethylthio, C₁-C₆-alkylsulfinyl such as, for example,                    methylsulfinyl and ethylsulfinyl,                    C₁-C₆-alkylsulfonyl such as, for example,                    methylsulfonyl, ethylsulfonyl and propylsulfonyl, or                    C₁-C₆-haloalkylsulfonyl such as, for example,                    trifluoromethylsulfonyl and                    pentafluoroethylsulfonyl.        -   Also especially preferred are 3-heterocyclyl-substituted            benzoyl derivatives of the formula I where            -   X is S, NR⁹, CO or CR¹⁰OR¹¹;            -   or            -   Y is O, S, NR¹² or CO.            -   Particularly preferred are 3-heterocyclyl-substituted                benzoyl derivatives of the formula I where R¹⁸ is                hydrogen.            -   Also particularly preferred are                3-heterocyclyl-substituted benzoyl derivatives of the                formula I where R¹⁸ is C₁-C₆-alkyl.                -   Extraordinarily preferred are                    3-heterocyclyl-substituted benzoyl derivatives of                    the formula I where                -    R⁴ is halogen, cyano, nitro, C₁-C₄-alkyl,                    C₁-C₄-alkoxy-C₁-C₄-alkyl,                    C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,                    C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-haloalkyl,                    C₁-C₄-cyanoalkyl, C₃-C₈-cycloalkyl, C₁-C₆-alkoxy,                    C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,                    C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,                    di(C₁-C₄-alkyl)amino, COR⁶, phenyl or benzyl, it                    being possible for the two last-mentioned                    substituents to be partially or fully halogenated                    and/or to have attached to them one to three of the                    following groups:                -    nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl,                    C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;                -    R⁵ is hydrogen or C₁-C₄-alkyl;                -    or                -    R⁴ and R⁵ together form a C₂-C₆-alkanediyl chain                    which can be mono- to tetrasubstituted by                    C₁-C₄-alkyl and/or which can be interrupted by                    oxygen or by a nitrogen which is unsubstituted or                    substituted by C₁-C₄-alkyl;                -    or                -    R⁴ and R⁹ or R⁴ and R¹⁰ or R⁵ and R¹² or R⁵ and R¹³                    together form a C₂-C₆-alkanediyl chain which can be                    mono- to tetrasubstituted by C₁-C₄-alkyl and/or                    which can be interrupted by oxygen or by a nitrogen                    which is unsubstituted or substituted by                    C₁-C₄-alkyl.            -   Also particularly preferred are                3-heterocyclyl-substituted benzoyl derivatives of the                formula I where                -   X is S, NR⁹ or CO                -   or                -   y is O, NR¹² or CO.                -   Extraordinarily preferred are                    3-heterocyclyl-substituted benzoyl derivatives of                    the formula I where                -    R⁴ is halogen, cyano, nitro, C₁-C₄-alkyl,                    C₁-C₄-alkoxy-C₁-C₄-alkyl,                    C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl,                    C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-haloalkyl,                    C₁-C₄-cyanoalkyl, C₃-C₈-cycloalkyl, C₁-C₆-alkoxy,                    C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,                    C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,                    di(C₁-C₄-alkyl)amino, COR⁶, phenyl or benzyl, it                    being possible for the two last-mentioned                    substituents to be partially or fully halogenated                    and/or to have attached to them one to three of the                    following groups:                -    nitro, cyano, C₁-C₄-Alkyl, C₁-C₄-haloalkyl,                    C₁-C₄-alkoxy or C₁-C₄-haloalkoxy;                -    R⁵ is hydrogen or C₁-C₄-alkyl;                -    or                -    R⁴ and R⁵ together form a C₂-C₆-alkanediyl chain                    which can be mono- to tetrasubstituted by                    C₁-C₄-alkyl and/or which can be interrupted by                    oxygen or by a nitrogen which is unsubstituted or                    substituted by C₁-C₄-alkyl;                -    or                -    R⁴ and R⁹ or R⁴ and R¹⁰ or R⁵ and R¹² or R⁵ and R¹³                    together form a C₂-C₆-alkanediyl chain which can be                    mono- to tetrasubstituted by C₁-C₄-alkyl and/or                    which can be interrupted by oxygen or by a nitrogen                    which is unsubstituted or substituted by                    C₁-C₄-alkyl.

Particularly extraordinarily preferred are the compounds Ia1({circumflex over (=)}I where R¹═Cl, R²═SO₂CH₃, R³═H, R¹⁶, R¹⁸═CH₃,Z=H), in particular the compounds of Table 1. TABLE 1 Ia1

No. X R⁴ R⁵ Y Ia1.1 CH₂ H CH₃ O Ia1.2 CH₂ H H O Ia1.3 C(CH₃)₂ H H OIa1.4 CH₂ H C₂H₅ O Ia1.5 CH₂ CH₃ CH₃ O Ia1.6 CH(CH₃) H CH₃ O Ia1.7CH(C₂H₅) H CH₃ O Ia1.8 CH[CH(CH₃)₂] H H O Ia1.9 CH₂ H CH(CH₃)₂ O Ia1.10CH(C₂H₅) H C₂H₅ O Ia1.11 —CH—(CH₂)₄— H O Ia1.12 C═O CH₃ CH₃ O Ia1.13 C═OH C₂H₅ O Ia1.14 C═O C₂H₅ C₂H₅ O Ia1.15 C═O H H O Ia1.16 C═O H CH₃ OIa1.17 CH₂ H CH₃ S Ia1.18 C(CH₃)₂ H H S Ia1.19 CH₂ H C₂H₅ S Ia1.20 CH₂CH₃ CH₃ S Ia1.21 CH(CH₃) H CH₃ S Ia1.22 CH(C₂H₅) H CH₃ S Ia1.23 CH(C₂H₅)H C₂H₅ S Ia1.24 —CH—(CH₂)₄— H S Ia1.25 CH[CH(CH₃)₂] H H S Ia1.26 CH₂ HCH(CH₃)₂ S Ia1.27 CH₂ H CH₃ NH Ia1.28 CH₂ H H NH Ia1.29 C(CH₃)₂ H H NHIa1.30 CH₂ H C₂H₅ NH Ia1.31 CH₂ CH₃ CH₃ NH Ia1.32 CH(CH₃) H CH₃ NHIa1.33 CH(C₂H₅) H CH₃ NH Ia1.34 CH(C₂H₅) H C₂H₅ NH Ia1.35 —CH—(CH₂)₄— HNH Ia1.36 CH[CH(CH₃)₂] H H NH Ia1.37 CH₂ H CH(CH₃)₂ NH Ia1.38 CH₂ H CH₃NCH₃ Ia1.39 CH₂ H H NCH₃ Ia1.40 C(CH₃)₂ H H NCH₃ Ia1.41 CH₂ H C₂H₅ NCH₃Ia1.42 CH₂ CH₃ CH₃ NCH₃ Ia1.43 CH(CH₃) H CH₃ NCH₃ Ia1.44 CH(C₂H₅) H CH₃NCH₃ Ia1.45 CH[CH(CH₃)₂] H H NCH₃ Ia1.46 CH₂ H CH(CH₃)₂ NCH₃ Ia1.47CH(C₂H₅) H C₂H₅ NCH₃ Ia1.48 —CH—(CH₂)₄— H NCH₃ Ia1.49 CH₂ H CH₃ NC₂H₅Ia1.50 CH₂ H H NC₂H₅ Ia1.51 C(CH₃)₂ H H NC₂H₅ Ia1.52 CH₂ H C₂H₅ NC₂H₅Ia1.53 CH₂ CH₃ CH₃ NC₂H₅ Ia1.54 CH(CH₃) H CH₃ NC₂H₅ Ia1.55 CH(C₂H₅) HCH₃ NC₂H₅ Ia1.56 CH[CH(CH₃)₂] H H NC₂H₅ Ia1.57 CH₂ H CH(CH₃)₂ NC₂H₅Ia1.58 CH(C₂H₅) H C₂H₅ NC₂H₅ Ia1.59 —CH—(CH₂)₄— H NC₂H₅ Ia1.60 CH₂ ═O SIa1.61 CH(CH₃) ═O S Ia1.62 CH(C₂H₅) ═O S Ia1.63 CH[CH(CH₃)₂] ═O S Ia1.64C(CH₃)₂ ═O S Ia1.65 CCH₃(C₂H₅) ═O S Ia1.66 CCH₃[CH(CH₃)₂] ═O S Ia1.67CH₂ ═O NH Ia1.68 CH(CH₃) ═O NH Ia1.69 CH(C₂H₅) ═O NH Ia1.70 CH[CH(CH₃)₂]═O NH Ia1.71 C(CH₃)₂ ═O NH Ia1.72 CCH₃(C₂H₅) ═O NH Ia1.73 CCH₃[CH(CH₃)₂]═O NH Ia1.74 CH₂ ═O NCH₃ Ia1.75 CH(CH₃) ═O NCH₃ Ia1.76 CH(C₂H₅) ═O NCH₃Ia1.77 CH[CH(CH₃)₂] ═O NCH₃ Ia1.78 C(CH₃)₂ ═O NCH₃ Ia1.79 CCH₃(C₂H₅) ═ONCH₃ Ia1.80 CCH₃[CH(CH₃)₂] ═O NCH₃ Ia1.81 O COOCH₃ H CH₂ Ia1.82 OCOOC₂H₅ H CH₂ Ia1.83 O CONHCH₃ H CH₂ Ia1.84 O CON(CH₃)₂ H CH₂ Ia1.85 OCONHC₂H₅ H CH₂ Ia1.86 O CON(C₂H₅)₂ H CH₂ Ia1.87 O CH₃ H CH₂ Ia1.88 OC₂H₅ H CH₂ Ia1.89 O CH(CH₃)₂ H CH₂ Ia1.90 O COC₂H₅ H CH₂ Ia1.91 O CH₂CNH CH₂ Ia1.92 O CH₂N(CH₃)₂ H CH₂ Ia1.93 O CH₂CN═C(CH₃)₂ H CH₂ Ia1.94 OOH(OC₂H₅)₂ H CH₂ Ia1.95 O OH(OCH₃)₂ H CH₂ Ia1.96 O CH₃ CH₃ CH₂ Ia1.97 OCH₃ C₂H₅ CH₂ Ia1.98 O C₂H₅ C₂H₅ CH₂ Ia1.99 O —(CH₂)₄— CH₂ Ia1.100 O—(CH₂)₂—O—(CH₂)₂— CH₂ Ia1.101 O H —(CH₂)₃—OH— Ia1.102 O H —(CH₂)₄—OH—Ia1.103 O CH₃ H CHCH₃ Ia1.104 S ═O O Ia1.105 CH₂ ═S S Ia1.106 CH(CH₃) ═SS Ia1.107 CH(C₂H₅) ═S S Ia1.108 C(CH₃)₂ ═S S Ia1.109 O ═O NH Ia1.110 O═O NCH₃ Ia1.111 O CH₃ H NH Ia1.112 O C₂H₅ H NH Ia1.113 O CH₃ CH₃ NHIa1.114 O C₂H₅ C₂H₅ NH Ia1.115 O CH₃ H NCH₃ Ia1.116 O C₂H₅ H NCH₃Ia1.117 O CH₃ CH₃ NCH₃ Ia1.118 O C₂H₅ C₂H₅ NCH₃ Ia1.119 NH ═O NH Ia1.120NH ═O NCH₃ Ia1.121 NCH₃ ═O NH Ia1.122 NCH₃ ═O NCH₃ Ia1.123 NC₂H₅ ═O NHIa1.124 NC₂H₅ ═O NC₂H₅

In addition, the following benzoyl derivatives of the formula I areparticularly extraordinarily preferred:

-   -   The compounds Ia2.1-Ia2.124, which differ from the corresponding        compounds Ia1.1-Ia1.124 by the fact that R¹⁶ is ethyl and R¹⁸ is        hydrogen.

Also particularly extraordinarily preferred are the compounds Ib1({circumflex over (=)}I where R¹, R²═Cl, R³═H, R¹⁶, R¹⁸═CH₃, Z=H) inparticular the compounds of Table 2 TABLE 2 Ib1

No. X R⁴ R⁵ Y Ib1.1 CH₂ H CH₃ O Ib1.2 CH₂ H H O Ib1.3 C(CH₃)₂ H H OIb1.4 CH₂ H C₂H₅ O Ib1.5 CH₂ CH₃ CH₃ O Ib1.6 CH(CH₃) H CH₃ O Ib1.7CH(C₂H₅) H CH₃ O Ib1.8 CH[CH(CH₃)₂] H H O Ib1.9 CH₂ H CH(CH₃)₂ O Ib1.10CH(C₂H₅) H C₂H₅ O Ib1.11 —CH—(CH₂)₄— H O Ib1.12 C═O CH₃ CH₃ O Ib1.13 C═OH C₂H₅ O Ib1.14 C═O C₂H₅ C₂H₅ O Ib1.15 C═O H H O Ib1.16 C═O H CH₃ OIb1.17 CH₂ H CH₃ S Ib1.18 CH₂ H H S Ib1.19 C(CH₃)₂ H H S Ib1.20 CH₂ HC₂H₅ S Ib1.21 CH₂ CH₃ CH₃ S Ib1.22 CH(CH₃) H CH₃ S Ib1.23 CH(C₂H₅) H CH₃S Ib1.24 CH(C₂H₅) H C₂H₅ S Ib1.25 —CH—(CH₂)₄— H S Ib1.26 CH[CH(CH₃)₂] HH S Ib1.27 CH₂ H CH(CH₃)₂ S Ib1.28 CH₂ H CH₃ NH Ib1.29 CH₂ H H NH Ib1.30C(CH₃)₂ H H NH Ib1.31 CH₂ H C₂H₅ NH Ib1.32 CH₂ CH₃ CH₃ NH Ib1.33 CH(CH₃)H CH₃ NH Ib1.34 CH(C₂H₅) H CH₃ NH Ib1.35 CH(C₂H₅) H C₂H₅ NH Ib1.36—CH—(CH₂)₄— H NH Ib1.37 CH[CH(CH₃)₂] H H NH Ib1.38 CH₂ H CH(CH₃)₂ NHIb1.39 CH₂ H CH₃ NCH₃ Ib1.40 CH₂ H H NCH₃ Ib1.41 C(CH₃)₂ H H NCH₃ Ib1.42CH₂ H C₂H₅ NCH₃ Ib1.43 CH₂ CH₃ CH₃ NCH₃ Ib1.44 CH(CH₃) H CH₃ NCH₃ Ib1.45CH(C₂H₅) H CH₃ NCH₃ Ib1.46 CH[CH(CH₃)₂] H H NCH₃ Ib1.47 CH₂ H CH(CH₃)₂NCH₃ Ib1.48 CH(C₂H₅) H C₂H₅ NCH₃ Ib1.49 —CH—(CH₂)₄— H NCH₃ Ib1.50 CH₂ HCH₃ NC₂H₅ Ib1.51 CH₂ H H NC₂H₅ Ib1.52 C(CH₃)₂ H H NC₂H₅ Ib1.53 CH₂ HC₂H₅ NC₂H₅ Ib1.54 CH₂ CH₃ CH₃ NC₂H₅ Ib1.55 CH(CH₃) H CH₃ NC₂H₅ Ib1.56CH(C₂H₅) H CH₃ NC₂H₅ Ib1.57 CH[CH(CH₃)₂] H H NC₂H₅ Ib1.58 CH₂ H CH(CH₃)₂NC₂H₅ Ib1.59 CH(C₂H₅) H C₂H₅ NC₂H₅ Ib1.60 —CH—(CH₂)₄— H NC₂H₅ Ib1.61 CH₂═O S Ib1.62 CH(CH₃) ═O S Ib1.63 CH(C₂H₅) ═O S Ib1.64 CH[CH(CH₃)₂] ═O SIb1.65 C(CH₃)₂ ═O S Ib1.66 CCH₃(C₂H₅) ═O S Ib1.67 CCH₃[CH(CH₃)₂] ═O SIb1.68 CH₂ ═O NH Ib1.69 CH(CH₃) ═O NH Ib1.70 CH(C₂H₅) ═O NH Ib1.71CH[CH(CH₃)₂] ═O NH Ib1.72 C(CH₃)₂ ═O NH Ib1.73 CCH₃(C₂H₅) ═O NH Ib1.74CCH₃[CH(CH₃)₂] ═O NH Ib1.75 CH₂ ═O NCH₃ Ib1.76 CH(CH₃) ═O NCH₃ Ib1.77CH(C₂H₅) ═O NCH₃ Ib1.78 CH[CH(CH₃)₂] ═O NCH₃ Ib1.79 C(CH₃)₂ ═O NCH₃Ib1.80 CCH₃(C₂H₅) ═O NCH₃ Ib1.81 CCH₃[CH(CH₃)₂] ═O NCH₃ Ib1.82 O COOCH₃H CH₂ Ib1.83 O COOC₂H₅ H CH₂ Ib1.84 O CONHCH₃ H CH₂ Ib1.85 O CON(CH₃)₂ HCH₂ Ib1.86 O CONHC₂H₅ H CH₂ Ib1.87 O CON(C₂H₅)₂ H CH₂ Ib1.88 O CH₃ H CH₂Ib1.89 O C₂H₅ H CH₂ Ib1.90 O CH(CH₃)₂ H CH₂ Ib1.91 O COC₂H₅ H CH₂ Ib1.92O CH₂CN H CH₂ Ib1.93 O CH₂N(CH₃)₂ H CH₂ Ib1.94 O CH₂CN═C(CH₃)₂ H CH₂Ib1.95 O OH(OC₂H₅)₂ H CH₂ Ib1.96 O OH(OCH₃)₂ H CH₂ Ib1.97 O CH₃ CH₃ CH₂Ib1.98 O CH₃ C₂H₅ CH₂ Ib1.99 O C₂H₅ C₂H₅ CH₂ Ib1.100 O —(CH₂)₄— CH₂Ib1.101 O —(CH₂)₂—O—(CH₂)₂— CH₂ Ib1.102 O H —(CH₂)₃—OH— Ib1.103 O H—(CH₂)₄—OH— Ib1.104 O CH₃ H CHCH₃ Ib1.105 O H H CH₂ Ib1.106 S ═O OIb1.107 CH₂ ═S S Ib1.108 CH(CH₃) ═S S Ib1.109 CH(C₂H₅) ═S S Ib1.110C(CH₃)₂ ═S S Ib1.111 O ═O NH Ib1.112 O ═O NCH₃ Ib1.113 O CH₃ H NHIb1.114 O C₂H₅ H NH Ib1.115 O CH₃ CH₃ NH Ib1.116 O C₂H₅ C₂H₅ NH Ib1.117O CH₃ H NCH₃ Ib1.118 O C₂H₅ H NCH₃ Ib1.119 O CH₃ CH₃ NCH₃ Ib1.120 O C₂H₅C₂H₅ NCH₃ Ib1.121 NH ═O NH Ib1.122 NH ═O NCH₃ Ib1.123 NCH₃ ═O NH Ib1.124NCH₃ ═O NCH₃ Ib1.125 NC₂H₅ ═O NH Ib1.126 NC₂H₅ ═O NC₂H₅

In addition, the following 3-heterocyclyl-substituted benzoylderivatives of the formula I are particularly extraordinarily preferred:

The compounds Ib2.1-Ib2.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro.

The compounds Ib3.1-Ib3.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl and R² ismethylsulfonyl.

The compounds Ib4.1-Ib4.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact R¹ is hydrogen and R² ismethylsulfonyl.

The compounds Ib5.1-Ib5.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is trifluoromethyl and R² ismethylsulfonyl.

The compounds Ib6.1-Ib6.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl.

The compounds Ib7.1-Ib7.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro.

The compounds Ib8.1-Ib8.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is trifluoromethyl.

The compounds Ib9.1-Ib9.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylthio.

The compounds Ib10.1-Ib10.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfinyl.

The compounds Ib11.1-Ib11.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is trifluoromethylsulfonyl.

The compounds Ib12.1-Ib12.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy and R² ismethylsulfonyl.

The compounds Ib13.1-Ib13.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl.

The compounds Ib14.1-Ib14.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact R² is methylsulfonyl and R³ ismethyl.

The compounds Ib15.1-Ib15.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl and R³ ischlorine.

The compounds Ib16.1-Ib16.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl and R³ is chlorine.

The compounds Ib17.1-Ib17.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl and R³ is methyl.

The compounds Ib18.1-Ib18.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl.

The compounds Ib19.1-Ib19.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl and R² ishydrogen.

The compounds Ib20.1-Ib20.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact R¹ is methyl and R² is nitro.

The compounds Ib21.1-Ib21.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl and R¹⁸ ishydrogen.

The compounds Ib22.1-Ib22.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro and R¹⁸ ishydrogen.

The compounds Ib23.1-Ib23.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib24.1-Ib24.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is hydrogen, R² ismethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib25.1-Ib25.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is trifluoromethyl, R² ismethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib26.1-Ib26.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl and R¹⁸ ishydrogen.

The compounds Ib27.1-Ib27.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact R¹ is nitro and R¹⁸ is hydrogen.

The compounds Ib28.1-Ib28.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is trifluoromethyl and R¹⁸is hydrogen.

The compounds Ib29.1-Ib29.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylthio and R¹⁸ ishydrogen.

The compounds Ib30.1-Ib30.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfinyl and R¹⁸ ishydrogen.

The compounds Ib31.1-Ib31.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is trifluoromethylsulfonyland R¹⁸ is hydrogen.

The compounds Ib32.1-Ib32.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² ismethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib33.1-Ib33.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl and R¹⁸ ishydrogen.

The compounds Ib34.1-Ib34.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R³ ismethyl and R¹⁸ is hydrogen.

The compounds Ib35.1-Ib35.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R³ ischlorine and R¹⁸ is hydrogen.

The compounds Ib36.1-Ib36.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R³ is chlorine and R¹⁸ is hydrogen.

The compounds Ib37.1-Ib37.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R³ is methyl and R¹⁸ is hydrogen.

The compounds Ib38.1-Ib38.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl and R¹⁸ ishydrogen.

The compounds Ib39.1-Ib39.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² is hydrogenand R¹⁸ is hydrogen.

The compounds Ib40.1-Ib40.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² is nitro andR¹⁸ is hydrogen.

The compounds Ib41.1-Ib41.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro, R¹⁶ is ethyl andR¹⁸ is hydrogen.

The compounds Ib42.1-Ib42.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R¹⁶ is ethyl and R¹⁸ is hydrogen.

The compounds Ib43.1-Ib43.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is hydrogen, R² ismethylsulfonyl, R¹⁶ is ethyl and R¹⁸ is hydrogen.

The compounds Ib44.1-Ib44.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is trifluoromethyl, R² ismethylsulfonyl, R¹⁶ is ethyl and R¹⁸ is hydrogen.

The compounds Ib45.1-Ib45.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, R¹⁶ isethyl and R¹⁸ is hydrogen.

The compounds Ib46.1-Ib46.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, R¹⁶ is ethyl andR¹⁸ is hydrogen.

The compounds Ib47.1-Ib47.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is trifluoromethyl, R¹⁶ isethyl and R¹⁸ is hydrogen.

The compounds Ib48.1-Ib48.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylthio, R¹⁶ is ethyland R¹⁸ is hydrogen.

The compounds Ib49.1-Ib49.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfinyl, R¹⁶ isethyl and R¹⁸ is hydrogen.

The compounds Ib50.1-Ib50.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is trifluoromethylsulfonyl,R¹⁶ is ethyl and R¹⁸ is hydrogen.

The compounds Ib51.1-Ib51.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² ismethylsulfonyl, R¹⁶ is ethyl and R¹⁸ is hydrogen.

-   -   wherein    -   R¹⁹ is hydroxyl or C₁-C₆-alkoxy;    -   R¹ is C₁-C₆-alkyl;    -   R² is C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl;    -   R³ is hydrogen;    -   R⁴ and R⁵ are hydrogen or C₁-C₄-alkyl;    -   X is CR¹⁰R¹¹, wherein R¹⁰ and R¹¹ are hydrogen or C₁-C₄-alkyl,        and    -   Y is oxygen.

29. A process for the preparation of the 3-heterocyclyl-substitutedbenzoyl compound of the formula I defined in claim 28, which comprisesacylating a pyrazole of the formula II

-   -   with an activated carboxylic acid IIIα or with a carboxylic acid        IIIβ

The compounds Ib52.1-Ib52.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, R¹⁶ isethyl and R¹⁸ is hydrogen.

The compounds Ib53.1-Ib53.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R³ ismethyl, R¹⁶ is ethyl and R¹⁸ is hydrogen.

The compounds Ib54.1-Ib54.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R³ ischlorine, R¹⁶ is ethyl and R¹⁸ is hydrogen.

The compounds Ib55.1-Ib55.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R³ is chlorine, R¹⁶ is ethyl and R¹⁸ is hydrogen.

The compounds Ib56.1-Ib56.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R³ is methyl, R¹⁶ is ethyl and R¹⁸ is hydrogen.

The compounds Ib57.1-Ib57.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R¹⁶ is ethyl andR¹⁸ is hydrogen.

The compounds Ib58.1-Ib58.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² is hydrogen,R¹⁶ is ethyl and R¹⁸ is hydrogen.

The compounds Ib59.1-Ib59.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² is nitro, R¹⁶is ethyl and R¹⁸ is hydrogen.

The compounds Ib61.1-Ib61.126 [sic], which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R¹⁶ isn-propyl and R¹⁸ is hydrogen.

The compounds Ib61.1-Ib61.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro, R¹⁶ is n-propyland R¹⁸ is hydrogen.

The compounds Ib62.1-Ib62.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R¹⁶ is n-propyl and R¹⁸ is hydrogen.

The compounds Ib63.1-Ib63.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is hydrogen, R² ismethylsulfonyl, R¹⁶ is n-propyl and R¹⁸ is hydrogen.

The compounds Ib64.1-Ib64.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is trifluoromethyl, R² ismethylsulfonyl, R¹⁶ is n-propyl and R¹⁸ is hydrogen.

The compounds Ib65.1-Ib65.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, R¹⁶ isn-propyl and R¹⁸ is hydrogen.

The compounds Ib66.1-Ib66.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, R¹⁶ is n-propyland R¹⁸ is hydrogen.

The compounds Ib67.1-Ib67.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is trifluoromethyl, R¹⁶ isn-propyl and R¹⁸ is hydrogen.

The compounds Ib68.1-Ib68.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylthio, R¹⁶ isn-propyl and R¹⁸ is hydrogen.

The compounds Ib69.1-Ib69.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfinyl, R¹⁶ isn-propyl and R¹⁸ is hydrogen.

The compounds Ib70.1-Ib70.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is trifluoromethylsulfonyl,R¹⁶ is n-propyl and R¹⁸ is hydrogen.

The compounds Ib71.1-Ib71.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² ismethylsulfonyl, R¹⁶ is n-propyl and R¹⁸ is hydrogen.

The compounds Ib72.1-Ib72.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, R¹⁶ isn-propyl and R¹⁸ is hydrogen.

The compounds Ib73.1-Ib73.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R³ ismethyl, R¹⁶ is n-propyl and R¹⁸ is hydrogen.

The compounds Ib74.1-Ib74.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R³ ischlorine, R¹⁶ is n-propyl and R¹⁸ is hydrogen.

The compounds Ib75.1-Ib75.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R³ is chlorine, R¹⁶ is n-propyl and R⁸ is hydrogen.

The compounds Ib76.1-Ib76.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R³ is methyl, R⁶ is n-propyl and R¹⁸ is hydrogen.

The compounds Ib77.1-Ib77.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R¹⁶ is n-propyland R¹⁸ is hydrogen.

The compounds Ib78.1-Ib78.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² is hydrogen,R¹⁶ is n-propyl and R¹⁸ is hydrogen.

The compounds Ib79.1-Ib79.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² is nitro, R¹⁶is n-propyl and R¹⁸ is hydrogen.

The compounds Ib80.1-Ib80.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹⁶ is n-propyl and R¹⁸ ishydrogen.

The compounds Ib81.1-Ib81.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R¹⁶ isn-butyl and R¹⁸ is hydrogen.

The compounds Ib82.1-Ib82.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro, R¹⁶ is n-butyl andR¹⁸ is hydrogen.

The compounds Ib83.1-Ib83.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R¹⁶ is n-butyl and R¹⁸ is hydrogen.

The compounds Ib84.1-Ib84.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is hydrogen, R² ismethylsulfonyl, R¹⁶ is n-butyl and R¹⁸ is hydrogen.

The compounds Ib85.1-Ib85.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is trifluoromethyl, R² ismethylsulfonyl, R¹⁶ is n-butyl and R¹⁸ is hydrogen.

The compounds Ib86.1-Ib86.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, R¹⁶ isn-butyl and R¹⁸ is hydrogen.

The compounds Ib87.1-Ib87.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, R¹⁶ is n-butyl andR¹⁸ is hydrogen.

The compounds Ib88.1-Ib88.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is trifluoromethyl, R¹⁶ isn-butyl and R¹⁸ is hydrogen.

The compounds Ib89.1-Ib89.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylthio, R¹⁶ isn-butyl and R¹⁸ is hydrogen.

The compounds Ib90.1-Ib90.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfinyl, R¹⁶ isn-butyl and R¹⁸ is hydrogen.

The compounds Ib91.1-Ib91.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is trifluoromethylsulfonyl,R¹⁶ is n-butyl and R¹⁸ is hydrogen.

The compounds Ib92.1-Ib92.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² ismethylsulfonyl, R¹⁶ is n-butyl and R¹⁸ is hydrogen.

The compounds Ib93.1-Ib93.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, R¹⁶ isn-butyl and R¹⁸ is hydrogen.

The compounds Ib94.1-Ib94.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R³ ismethyl, R¹⁶ is n-butyl and R¹⁸ is hydrogen.

The compounds Ib95.1-Ib95.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R³ ischlorine, R¹⁶ is n-butyl and R¹⁸ is hydrogen.

The compounds Ib96.1-Ib96.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R³ is chlorine, R¹⁶ is n-butyl and R¹⁸ is hydrogen.

The compounds Ib97.1Ib97.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R³ is methyl, R¹⁶ is n-butyl and R¹⁸ is hydrogen.

The compounds Ib98.1-Ib98.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R¹⁶ is n-butyland R¹⁸ is hydrogen.

The compounds Ib99.1-Ib99.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² is hydrogen,R¹⁶ is n-butyl and R¹⁸ is hydrogen.

The compounds Ib100.1-Ib100.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² is nitro, R¹⁶is n-butyl and R¹⁸ is hydrogen.

The compounds Ib101.1-Ib101.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹⁶ is n-butyl and R¹⁸ ishydrogen.

The compounds Ib102.1-Ib102.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R¹⁶ isiso-butyl and R¹⁸ is hydrogen.

The compounds Ib115.1-Ib115.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R³ ismethyl, R¹⁶ is iso-butyl and R¹⁸ is hydrogen.

The compounds Ib116.1-Ib116.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R³ ischlorine, R¹⁶ is iso-butyl and R¹⁸ is hydrogen.

The compounds Ib117.1-Ib117.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R³ is chlorine, R¹⁶ is iso-butyl and R¹⁸ is hydrogen.

The compounds Ib118.1-Ib118.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R³ is methyl, R¹⁶ is iso-butyl and R¹⁸ is hydrogen.

The compounds Ib119.1-Ib119.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R¹⁶ is iso-butyland R¹⁸ is hydrogen.

The compounds Ib120.1-Ib120.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² is hydrogen,R¹⁶ is iso-butyl and R¹⁸ is hydrogen.

The compounds Ib121.1-Ib121.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² is nitro, R¹⁶is iso-butyl and R¹⁸ is hydrogen.

The compounds Ib122.1-Ib122.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹⁶ is iso-butyl and R¹⁸ ishydrogen.

The compounds Ib123.1-Ib123.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact R¹ is methylsulfonyl and R² istrifluoromethyl.

The compounds Ib124.1-Ib124.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, R² istrifluoromethyl, and R¹⁸ is hydrogen.

The compounds Ib125.1-Ib125.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, R² istrifluoromethyl, R¹⁶ is n-propyl and R¹⁸ is hydrogen.

The compounds Ib126.1-Ib126.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, R² istrifluoromethyl, R¹⁶ is n-butyl and R¹⁸ is hydrogen.

The compounds Ib127.1-Ib127.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, R² istrifluoromethyl, R¹⁶ is iso-butyl and R¹⁸ is hydrogen.

The compounds Ib128.1-Ib128.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, R² istrifluoromethyl, R¹⁶ is ethyl and R¹⁸ is hydrogen.

The compounds Ib129.1-Ib129.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro and R² ismethylsulfonyl.

The compounds Ib130.1-Ib130.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, R² ismethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib131.1-Ib131.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, R² ismethylsulfonyl, R¹⁶ is n-propyl and R¹⁸ is hydrogen.

The compounds Ib132.1-Ib132.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, R² ismethylsulfonyl, R¹⁶ is n-butyl and R¹⁸ is hydrogen.

The compounds Ib133.1-Ib133.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, R² ismethylsulfonyl, R¹⁶ is iso-butyl and R¹⁸ is hydrogen.

The compounds Ib134.1-Ib134.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, R² ismethylsulfonyl, R¹⁶ is ethyl and R¹⁸ is hydrogen.

The compounds Ib135.1-Ib135.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹⁸ is hydrogen.

The compounds Ib136.1-Ib136.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹⁶ is ethyl and R¹⁸ ishydrogen.

The compounds Ib137.1-Ib137.126 which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that Z is methylsulfonyl and R¹⁸ ishydrogen.

The compounds Ib138.1-Ib138.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, Z ismethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib139.1-Ib139.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro, Z ismethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib140.1-Ib140.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, Z is methylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib141.1-Ib141.126 which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, Z ismethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib142.1-Ib142.126 which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, Z ismethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib143.1-Ib143.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact R¹ is methoxy, R² and Z aremethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib144.1-Ib144.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, Z ismethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib145.1-Ib145.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹⁶ is ethyl, Z ismethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib146.1-Ib146.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R¹⁶ isethyl, Z is methylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib147.1-Ib147.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro, R¹⁶ is ethyl, Z ismethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib148.1-Ib148.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R¹⁶ is ethyl, Z is methylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib149.1-Ib149.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, R¹⁶ isethyl, Z is methylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib150.1-Ib150.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, R¹⁶ is ethyl, Z ismethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib151.1-Ib151.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² ismethylsulfonyl, R¹⁶ is ethyl, Z is methylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib152.1-Ib152.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, R¹⁶ isethyl, Z is methylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib153.1-Ib153.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that Z is methylsulfonyl.

The compounds Ib154.1-Ib154.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² and Z are methylsulfonyl.

The compounds Ib155.1-Ib155.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro and Z ismethylsulfonyl.

The compounds Ib156.1-Ib156.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² and Z aremethylsulfonyl.

The compounds Ib157.1-Ib157.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ and Z are methylsulfonyl.

The compounds Ib158.1-Ib158.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro and Z ismethylsulfonyl.

The compounds Ib159.1-Ib159.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² and Z aremethylsulfonyl.

The compounds Ib160.1-Ib160.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl and Z ismethylsulfonyl.

The compounds Ib161.1-Ib161.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that Z is ethylsulfonyl and R¹⁸ ishydrogen.

The compounds Ib162.1-Ib162.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, Z isethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib163.1-Ib163.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro, Z is ethylsulfonyland R¹⁸ is hydrogen.

The compounds Ib164.1-Ib164.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, Z is ethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib165.1-Ib165.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, Z isethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib166.1-Ib166.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, Z is ethylsulfonyland R¹⁸ is hydrogen.

The compounds Ib167.1-Ib167.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² ismethylsulfonyl, Z is ethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib168.1-Ib168.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² and Z are ethylsulfonyl andR¹⁸ is hydrogen.

The compounds Ib169.1-Ib169.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹⁶ is ethyl, Z isethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib170.1-Ib170.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R¹⁶ isethyl, Z is ethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib171.1-Ib171.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro, R¹⁶ is ethyl, Z isethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib172.1-Ib172.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R¹⁶ is ethyl, Z is ethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib173.1-Ib173.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, R¹⁶ isethyl, Z is ethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib174.1-Ib174.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, R¹⁶ is ethyl, Z isethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib175.1-Ib175.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² ismethylsulfonyl, R¹⁶ is ethyl, Z is ethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib176.1-Ib176.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, R¹⁶ isethyl, Z is ethylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib177.1-Ib177.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that Z is ethylsulfonyl.

The compounds Ib178.1-Ib178.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl and Z isethylsulfonyl.

The compounds Ib179.1-Ib179.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro and Z isethylsulfonyl.

The compounds Ib180.1-Ib180.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl and Z is ethylsulfonyl.

The compounds Ib181.1-Ib181.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl and Z isethylsulfonyl.

The compounds Ib182.1-Ib182.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro and Z isethylsulfonyl.

The compounds Ib183.1-Ib183.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² ismethylsulfonyl and Z is ethylsulfonyl.

The compounds Ib184.1-Ib184.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² and Z are ethylsulfonyl.

The compounds Ib185.1-Ib185.126 which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that Z is iso-propylsulfonyl and R¹⁸is hydrogen.

The compounds Ib186.1-Ib186.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, Z isiso-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib199.1-Ib199.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² ismethylsulfonyl, R¹⁶ is ethyl, Z is iso-propylsulfonyl and R¹⁸ ishydrogen.

The compounds Ib200.1-Ib200.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, R¹⁶ isethyl, Z is iso-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib201.1-Ib201.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that Z is n-propylsulfonyl and R¹⁸is hydrogen.

The compounds Ib202.1-Ib202.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, Z isn-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib203.1-Ib203.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro, Z isn-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib204.1-Ib204.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, Z is n-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib205.1-Ib205.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, Z isn-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib206.1-Ib206.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, Z isn-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib207.1-Ib207.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² ismethylsulfonyl, Z is n-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib.208.1-Ib208.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, Z isn-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib209.1-Ib209.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹⁶ is ethyl, Z isn-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib210.1-Ib210.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R¹⁶ isethyl, Z is n-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib211.1-211.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro, R¹⁶ is ethyl, Z isn-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib212.1-Ib212.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R¹⁶ is ethyl, Z is n-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib213.1-Ib213.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, R¹⁶ isethyl, Z is n-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib214.1-Ib214.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, R¹⁶ is ethyl, Z isn-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib215.1-Ib215.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² ismethylsulfonyl, R¹⁶ is ethyl, Z is n-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib216.1-Ib216.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, R¹⁶ isethyl, Z is n-propylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib217.1-Ib217.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that Z is n-butylsulfonyl and R¹⁸ ishydrogen.

The compounds Ib218.1-Ib218.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, Z isn-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib219.1-Ib219.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro, Z isn-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib220.1-Ib220.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, Z is n-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib221.1-Ib221.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, Z isn-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib222.1-Ib222.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, Z isn-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib223.1-Ib223.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² ismethylsulfonyl, Z is n-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib224.1-Ib224.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, Z isn-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib225.1-Ib225.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹⁶ is ethyl, Z isn-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib226.1-Ib226.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R¹⁶ isethyl, Z is n-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib227.1-Ib227.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro, R¹⁶ is ethyl, Z isn-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib228.1-Ib228.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R¹⁶ is ethyl, Z is n-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib229.1-Ib229.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, R¹⁶ isethyl, Z is n-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib230.1-Ib230.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, R¹⁶ is ethyl, Z isn-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib231.1-Ib231.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² ismethylsulfonyl, R¹⁶ is ethyl, Z is n-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib232.1-Ib232.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, R¹⁶ isethyl, Z is n-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib233.1-Ib233.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that Z is iso-butylsulfonyl and R¹⁸is hydrogen.

The compounds Ib234.1-Ib234.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, Z isiso-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib235.1-Ib235.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro, Z isiso-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib236.1-Ib236.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, Z is iso-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib237.1-Ib237.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, Z isiso-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib238.1-Ib238.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, Z isiso-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib239.1-Ib239.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² ismethylsulfonyl, Z is iso-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib240.1-Ib240.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, Z isiso-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib241.1-Ib241.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹⁶ is ethyl, Z isiso-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib242.1-Ib242.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R¹⁶ isethyl, Z is iso-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib243.1-Ib243.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is nitro, R¹⁶ is ethyl, Z isiso-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib244.1-Ib244.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R¹⁶ is ethyl, Z is iso-butylsulfonyl and R¹⁸ ishydrogen.

The compounds Ib245.1-Ib245.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methylsulfonyl, R¹⁶ isethyl, Z is iso-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib246.1-Ib246.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is nitro, R¹⁶ is ethyl, Z isiso-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib247.1-Ib247.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methoxy, R² ismethylsulfonyl, R¹⁶ is ethyl, Z is iso-butylsulfonyl and R¹⁸ ishydrogen.

The compounds Ib248.1-Ib248.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R¹⁶ isethyl, Z is iso-butylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib249.1-Ib249.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that Z is phenylsulfonyl and R¹⁸ ishydrogen.

The compounds Ib250.1-Ib250.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, Z isphenylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib251.1-Ib251.126 which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, Z is phenylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib252.1-Ib252.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, Z isphenylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib253.1-Ib253.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹⁶ is ethyl, Z isphenylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib254.1-Ib254.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R¹⁶ isethyl, Z is phenylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib255.1-Ib255.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R¹⁶ is ethyl, Z is phenylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib256.1-Ib256.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, R¹⁶ isethyl, Z is phenylsulfonyl and R¹⁸ is hydrogen.

The compounds Ib257.1-Ib257.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that Z is p-toluenesulfonyl and R¹⁸is hydrogen.

The compounds Ib258.1-Ib258.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, Z isp-toluenesulfonyl and R¹⁸ is hydrogen.

The compounds Ib259.1-Ib259.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, Z is p-toluenesulfonyl and R¹⁸ is hydrogen.

The compounds Ib260.1-Ib260.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, Z isp-toluenesulfonyl and R¹⁸ is hydrogen.

The compounds Ib261.1-Ib261.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹⁶ is ethyl, Z isp-toluenesulfonyl and R¹⁸ is hydrogen.

The compounds Ib262.1-Ib262.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is methylsulfonyl, R¹⁶ isethyl, Z is p-toluenesulfonyl and R¹⁸ is hydrogen.

The compounds Ib263.1-Ib263.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R¹ is methyl, R² ismethylsulfonyl, R¹⁶ is ethyl, Z is p-toluenesulfonyl and R¹⁸ ishydrogen.

The compounds Ib264-Ib264.126, which differ from the correspondingcompounds Ib1.1-Ib1.126 by the fact that R² is ethylsulfonyl, R¹⁶ isethyl, Z is p-toluenesulfonyl and R¹⁸ is hydrogen.

Also particularly preferred are 3-heterocyclyl-substituted benzoylderivatives of the formula I where:

-   -   R¹ is halogen, C₁-C₆-alkyl, C₁-C₆-alkylthio or        C₁-C₆-alkylsulfonyl;        -   in particular chlorine, methyl, methylthio or            methylsulfonyl;    -   R² is hydrogen, nitro, halogen, C₁-C₆-alkylthio,        C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl;        -   in particular hydrogen, nitro, chlorine, methylthio,            methylsulfinyl, methylsulfonyl, ethylsulfonyl or            propylsulfonyl;    -   R³ is hydrogen;    -   R⁴, R⁵ are hydrogen, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy, C₁-C₄-alkylthio or COR⁶;        -   in particular hydrogen, fluorine, methyl, ethyl, propyl,            trifluoromethyl, chloromethyl, 1-chloroeth-1-yl, methoxy,            ethoxy, ethylthio or ethoxycarbonyl;    -   or    -   R⁴ and R⁵ together form a C₂-C₆-alkanediyl chain which can be        mono- to polysubstituted by C₁-C₄-alkyl and/or which can be        interrupted by oxygen or by a nitrogen which is unsubstituted or        substituted [lacuna] C₁-C₄-alkyl;    -   R⁶ is C₁-C₄-alkoxy;        -   in particular ethyl;    -   X is O or CR¹⁰R¹¹;    -   Y is O, S or CR¹³R¹⁴;    -   R¹⁰, R¹¹, R¹³, R¹⁴ are hydrogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl;        in particular hydrogen, methyl or chloromethyl;    -   or    -   R⁵ and R¹³ together form a C₂-C₆-alkanediyl chain which can be        mono- to polysubstituted by C₁-C₄-alkyl and/or which can be        interrupted by oxygen or by a nitrogen which is unsubstituted or        substituted [lacuna] C₁-C₄-alkyl; in particular 1,3-propdiyl        [sic];    -   R¹⁶ is C₁-C₆-alkyl;        -   in particular methyl, ethyl, propyl, 2-methylpropyl or            butyl;    -   Z is H or SO₂R¹⁷;    -   R¹⁷ is C₁-C₄-alkyl;        -   in particular methyl, ethyl, propyl or 2-methylpropyl;

with the exception of4-[2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-ethyl-5-hydroxy-1H-pyrazole,4-[2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-benzoyl]-1,3-dimethyl-5-hydroxy-1H-pyrazole,4-[2-chloro-3-(5-cyano-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-1,3-dimethyl-5-hydroxy-1H-pyrazoleand4-[2-chloro-3-(4,5-dihydrothiazol-2-yl)-4-methylsulfonylbenzoyl]-1,3-dimethyl-5-hydroxy-1H-pyrazole;

and the agriculturally useful salts thereof;

in particular alkali metal salts and ammonium salts.

The 3-heterocyclyl-substituted benzoyl derivatives of the formula I areobtainable by various routes, for example by the following process:

Process A:

Reaction of pyrazoles of the formula II (where Z=H) with an activatedbenzoic acid IIIα or a benxoic acid IIIβ, which is preferably activatedin situ to give the acylating product and subsequently subjecting thelatter to a rearrangement reaction.

L¹ is a nucleophilically displaceable leaving group such as halogen, eg.bromine, chlorine, hetaryl, eg. imidazolyl, pyridyl, carboxylate, eg.acetate, trifluoroacetate, and the like.

The activated benzoic acid can be employed directly, as in the case ofthe benzoyl halides, or it can be prepared in situ, for example withdicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic ester,2-pyridine disulfide/triphenylphosphine, carbonyldiimidazole and thelike.

It may be advantageous to carry out the acylation reaction in thepresence of a base. The reactants and the auxiliary base are expedientlyemployed in equimolar amounts. A small excess of the auxiliary base, forexample 1.2 to 1.5 mol equivalents based on II, may be advantageousunder certain circumstances.

Suitable auxiliary bases are tertiary alkylamines, pyridine or alkalimetal carbonates. Examples of solvents which can be used are chlorinatedhydrocarbons such as methylene chloride, 1,2-dichloroethane, aromatichydrocarbons such as toluene, xylene, chlorobenzene, ethers such asdiethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polaraprotic solvents such as acetonitrile, dimethylformamide, dimethylsulfoxide, or esters such as ethyl acetate, or mixtures of these.

If benzoyl halides are employed as activated carboxylic acid component,it may be expedient to cool the reaction mixture to 0-10° C. when addingthis reactant. The mixture is subsequently stirred at 20-100° C.,preferably at 25-50° C., until the reaction is complete. Work-up iscarried out in the customary manner, for example the reaction mixture ispoured into water and the product of value is extracted. Especiallysuitable solvents for this purpose are methylene chloride, diethyl etherand ethyl acetate. After the organic phase has been dried and thesolvent removed, the crude ester can be employed without furtherpurification for the rearrangement reaction.

Rearrangement of the esters to give the compounds of the formula I isexpediently carried out at from 20 to 40° C. in a solvent and in thepresence of a base and, if appropriate, with the aid of a cyano compoundas catalyst.

Examples of solvents which can be used are acetonitrile, methylenechloride, 1,2-dichlorethane, dioxane, ethyl acetate, toluene or mixturesof these. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines such triethylamine, pyridine, oralkali metal carbonates such as sodium carbonate, potassium carbonate,all of which are preferably employed in equimolar amounts or up to afourfold excess, based on the ester. Triethylamine or alkali metalcarbonate are preferably used, but by preference in a ratio of twice theequimolar amount based on the ester.

Suitable cyano compounds are inorganic cyanides such as sodium cyanide,potassium cyanide, and organic cyano compounds such as acetonecyanohydrin, trimethylsily cyanide. They are employed in an amount offrom 1 to 50 mol percent, based on the ester. Substances which arepreferably employed are acetone cyanohydrin or trimethylsilyl cyanide,for example in an amount of from 5 to 15, preferably 10, mol percent,based on the ester.

Work-up can be effected in a manner known per se. For example, thereaction mixture is acidified with dilute mineral acid, such as 5%strength hydrochloric acid or sulfuric acid, and extracted with anorganic solvent, eg. methylene chloride or ethyl acetate. The organicextract can be extracted with 5-10% strength alkali metal carbonatesolution, eg. sodium carbonate or potassium carbonate solution. Theaqueous phase is acidified, and the precipitate which forms is filteredoff with suction and/or extracted with methylene chloride or ethylacetate, dried and concentrated. (Examples of the synthesis of estersfrom hydroxypyrazoles and of the rearrangement of the esters arementioned, for example, in EP-A 282 944 and U.S. Pat. No. 4,643,757).

Process B:

Reaction of 3-heterocyclyl-substituted benzoyl derivatives of theformula I (where Z=H) with a compound of the formula V (where Z=SO₂R¹⁷)

L² is a nucleophilically displaceable leaving group, such as halogen,eg. bromine, chlorine, hetaryl, eg. imidazolyl, pyridyl, sulfonate, eg.OSO₂R¹⁷.

The compounds of the formula V can be employed directly such as, forexample, in the case of the sulfonyl halides or sulfonic anhydrides, orthey can be prepared in situ, for example activated sulfonic acids (bymeans of sulfonic acid and dicyclohexylcarbodiimide, carbonyldiimidazoleand the like).

As a rule, the starting compounds are employed in an equimolar ratio.However, it may also be advantageous to employ an excess of one or theother component.

It may be advantageous to carry out the reaction in the presence of abase. The reactants and the auxiliary base are expediently employed inequimolar ratios. An excess of the auxiliary base, for example 1.5 to 3mol equivalents, based on II, may be advantageous under certaincircumstances.

Suitable auxiliary bases are tertiary alkylamines such as triethylamineor pyridine, alkali metal carbonates, eg. sodium carbonate or potassiumcarbonate, and alkali metal hydrides, eg. sodium hydride. Triethylamineand pyridine are preferably used.

Examples of suitable solvents are chlorinated hydrocarbons such asmethylene chloride or 1,2-dichlorethane, aromatic hydrocarbons, eg.toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyltert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solventssuch as acetonitrile, dimethylformamide or dimethyl sulfoxide, or esterssuch as ethyl acetate, or mixtures of these.

As a rule, the reaction temperature is in the range of from 0° C. to theboiling point of the reaction mixture.

Work-up can be effected in a manner known per se to give the product.

Those pyrazoles of the formula II (where Z=H) which are used as startingmaterials and which are not already known can be prepared by processesknown per se (for example EP-A 240 001 and J. Prakt. Chem. 315, 383(1973)).

Novel 3-heterocyclyl-substituted benzoic acid derivatives of the formulaIII

are those where the variables have the following meanings:

-   -   R¹, R² are hydrogen, nitro, halogen, cyano, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, C₁-C₆-alkylsulfinyl,        C₁-C₆-haloalkylsulfinyl, C₁-C₆-alkylsulfonyl or        C₁-C₆-haloalkylsulfonyl;    -   R³ is hydrogen, halogen or C₁-C₆-alkyl;    -   R⁴, R⁵ are hydrogen, halogen, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₄-alkyl, di(C₁-C₄-alkoxy)-C₁-C₄-alkyl,        di(C₁-C₄-alkyl)amino-C₁-C₄-alkyl,        [2,2-di(C₁-C₄-alkyl)hydrazino-1]-C₁-C₄-alkyl,        C₁-C₆-alkyliminooxy-C₁-C₄-alkyl,        C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,        C₁-C₄-haloalkyl, C₁-C₄-cyanoalkyl, C₃-C₈-cycloalkyl,        C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₂-C₄-alkoxy, C₁-C₄-haloalkoxy,        hydroxyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkylthio,        C₁-C₄-haloalkylthio, di(C₁-C₄-alkyl)amino, COR⁶, phenyl or        benzyl, it being possible for the two last-mentioned        substituents to be partially or fully halogenated and/or to have        attached to them one to three of the following groups: nitro,        cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or        C₁-C₄-haloalkoxy;    -   or    -   R⁴ and R⁵ together form a C₂-C₆-alkanediyl chain which can be        mono- to tetrasubstituted by C₁-C₄-alkyl and/or which can be        interrupted by oxygen or by a nitrogen which is unsubstituted or        substituted by C₁-C₄-alkyl;    -   or    -   R⁴ and R⁵ together with the corresponding carbon form a carbonyl        or a thiocarbonyl group;    -   R⁶ is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,        C₁-C₄-alkoxy-C₂-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₆-alkenyloxy,        C₃-C₆-alkynyloxy or NR⁷R⁸;    -   R⁷ is hydrogen or C₁-C₄-alkyl;    -   R⁸ is C₁-C₄-alkyl;    -   X is O, S, NR⁹, CO or CR¹⁰R¹¹;    -   Y Y is O, S, NR¹², CO or CR¹³R¹⁴;    -   R⁹, R¹² are hydrogen or C₁-C₄-alkyl;    -   R¹⁰, R¹¹, R¹³, R¹⁴ are hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxycarbonyl, C₁-C₄-haloalkoxycarbonyl or CONR⁷R⁸;    -   or    -   R⁴ and R⁹ or R⁴ and R¹⁰ or R⁵ and R¹² or R⁵ and R¹³ together        form a C₂-C₆-alkanediyl chain which can be mono- to        tetrasubstituted by C₁-C₄-alkyl and/or which can be interrupted        by oxygen or by a nitrogen which is unsubstituted or substituted        by C₁-C₄-alkyl;    -   R¹⁹ is hydroxyl or a radical which can be removed by hydrolysis;

with the exception of methyl2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate, methyl2-chloro-3-(4,5-dihydrooxazol-2-yl)-4-methylsulfonylbenzoate and methyl2,4-dichloro-3-(5-methylcarbonyloxy-4,5-dihydroisoxazol-3-yl)-benzoate.

Examples of radicals which can be removed by hydrolysis are alkoxy,phenoxy, alkylthio and phenylthio radicals which are unsubstituted orsubstituted, halides, hetaryl radicals which are bonded via nitrogen;amino, imino radicals which are unsubstituted or substituted, and thelike.

Preferred are 3-heterocyclyl-substituted benzoic acid halides of theformula IIIα′, where L^(1′)=halogen ({circumflex over (=)}III whereR¹⁹=halogen)

where the variables R¹ to R⁵, X and Y have the meanings given under theformula III and

-   -   L^(1′) is halogen, in particular chlorine or bromine.

Equally preferred are 3-heterocyclyl-substituted benzoic acids of theformula IIIβ ({circumflex over (=)}III where R¹⁹=hydroxyl)

where the variables R¹ to R⁵, X and Y have the meanings given underformula III.

Equally preferred are 3-heterocyclyl-substituted benzoic esters of theformula IIIγ ({circumflex over (=)}III where R¹⁹═C₁-C₆-alkoxy)

where the variables R¹ to R⁵, X and Y have the meanings given underformula III and

-   -   L³ is C₁-C₆-alkoxy.

The specially preferred embodiments of the 3-heteroacyclyl-substitutedbenzoic acid derivatives of the formula III with regard to the variablesR¹ to R⁵, X and Y correspond to those of the 3-heterocyclyl-substitutedbenzoyl derivatives of the formula I.

Also preferred are 3-heterocyclyl-substituted benzoic acid derivativesof the formula III, where:

-   -   R¹ is halogen, C₁-C₆-alkyl, C₁-C₆-alkylthio or        C₁-C₆-alkylsulfonyl;        -   in particular chlorine, methyl, methylthio or            methylsulfonyl;        -   extraordinarily preferably chlorine;    -   R² is hydrogen, nitro, halogen, C₁-C₆-alkylthio,        C₁-C₆-alkylsulfinyl or C₁-C₆-alkylsulfonyl;        -   in particular hydrogen, nitro, chlorine, methylthio,            methylsulfinyl, methylsulfonyl, ethylsulfonyl or            propylsulfonyl;        -   extraordinarily preferably hydrogen, chlorine, methylthio,            methylsulfonyl, ethylsulfonyl or propylsulfonyl;    -   R³ is hydrogen;    -   R⁴, R⁵ are hydrogen, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₁-C₄-alkoxy, hydroxyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkylthio        or COR⁶;        -   in particular hydrogen, fluorine, methyl, ethyl, propyl,            trifluoromethyl, chloromethyl, 2-chloroeth-1-yl, methoxy,            ethoxy, 2-methylprop-1-oxy, hydroxyl, methylcarbonyloxy,            ethylthio, formyl, methylcarbonyl, methoxycarbonyl or            ethoxycarbonyl;        -   extraordinarily preferably hydrogen, fluorine, methyl,            ethyl, trifluoromethyl, chloromethyl, 2-chloroeth-1-yl,            methoxy, ethoxy, 2-methylprop-1-oxy, hydroxyl,            methylcarbonyloxy, ethylthio, formyl, methylcarbonyl,            methoxycarbonyl or ethoxycarbonyl;    -   or    -   R⁴ and R⁵ together form a C₂-C₆-alkanediyl chain which can be        mono- to polysubstituted by C₁-C₄-alkyl and/or which can be        interrupted by oxygen or by a nitrogen which is unsubstituted or        substituted by C₁-C₄-alkyl;        -   in particular 1,4-butdiyl, 2-oxo-1,5-pentdiyl;    -   or    -   R⁴ and R⁵ together with the corresponding carbon atoms form a        carbonyl group    -   R⁶ is hydrogen, C₁-C₄-alkyl or C₁-C₄-alkoxy;        -   in particular hydrogen, methyl, methoxy or ethoxy;    -   X is O, S, CO, CR¹⁰R¹¹;    -   Y is O, S, CR¹³R¹⁴;    -   R¹⁰, R¹¹, R¹³, R¹⁴ are hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or        C₁-C₄-alkoxycarbonyl;        -   in particular hydrogen, methyl, chloromethyl or            methoxycarbonyl;    -   or    -   R⁵ and R¹³ together form a C₂-C₆-alkanediyl chain which can be        mono- to polysubstituted by C₁-C₄-alkyl and/or which can be        interrupted by oxygen or by a nitrogen which is unsubstituted or        substituted by C₁-C₄-alkyl;        -   in particular 1,3-propdiyl;    -   R¹⁹ is hydroxyl, halogen or C₁-C₆-alkoxy;        -   in particular hydroxyl, chlorine, methoxy or ethoxy;

with the exception of methyl2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate, methyl2-chloro-3-(4,5-dihydro-oxazol-2-yl)-4-methylsulfonylbenzoate and methyl2,4-dichloro-3-(5-methylcarbonyloxy-4,5-dihydroisoxazol-3-yl)benzoate.

The benzoyl halides of the formula IIIα′ (where L^(1′)=Cl, Br) can beprepared in a manner known per se by reacting the benzoic acids of theformula IIIβ with halogenating reagents such as thionyl chloride,thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride oroxalyl bromide.

The benzoic acids of the formula IIIβ can be prepared in a known mannerfrom the corresponding esters of the formula IIIγ (L³=C₁-C₆-alkoxy) bymeans of acid or basic hydrolysis.

Equally, the benzoic acids of the formula IIIβ can be obtained byreacting corresponding bromine- or iodine-substituted compounds of theformula V, with carbon monoxide and water under elevated pressure in thepresence of a palladium, nickel, cobalt or rhodium transition metalcatalyst and a base.

Furthermore, it is possible to convert compounds of the formula V intothe corresponding nitrites of the formula VI by a Rosenmund-von Braunreaction (cf., for example, Org. Synth. Vol III (1955), 212) and toconvert these nitrites into the compounds of the formula IIIβ bysubsequent hydrolysis.

The esters of the formula IIIγ can be obtained by reacting arylhalogencompounds or arylsulfonates of the formula VII, where L⁴ is a leavinggroup such as bromine, iodine, triflate, fluorosulfonyloxy and the likewith heterocyclyl stannates (Stille couplings), heterocyclyl-boroncompounds (Suzuki couplings) or heterocyclyl-zinc compounds (Negishireaction) VIII, where M is Sn(C₁-C₄-alkyl)₃, B(OH)₂, ZnHal (whereHal=chlorine, bromine) and the like, respectively, in a manner known perse (cf., for example, Tetrahedron Lett. 27 (1986), 5269) in the presenceof a palladium or nickel transition metal catalyst and in the presenceor absence of a base.

Equally, it is possible to obtain esters of the formula IIIγ bysynthesizing the heterocycle which is bonded in the 3-position.

For example, 1,2,4-oxadiazolin-3-yl derivatives (IIIγ where X═O, Y═NH)can be prepared from amidoximes of the formula IX by condensation withaldehydes or ketones (cf., for example, Arch. Phar. 326 (1993),383-389).

Thioamides of the formula X are suitable precursors for 2-thiazolinylderivatives I (where X═CR¹⁰R¹¹, Y═S) (cf., for example, Tetrahedron 42(1986), 1449-1460).

2-Oxazolinyl, 2-thiazolinyl and 2-imidazolinyl derivatives (IIIγ whereX═CR¹⁰R¹¹, Y═O or Y═S or Y═NH) are accessible from the carboxylic acidsof the formula XI (cf., for example, Tetrahedron Let. 22 (1981),4471-4474).

1,3-Thiazol-5(4H)-thion-2-yl (cf., for example, Helv. Chim. Acta 69(1986), 374-388) and 5-oxo-2-imidazolin-2-yl derivatives (cf., forexample, Heterocycles 29 (1989), 1185-1189) (III where X═CR¹⁰OR¹¹, Y═Sor Y═NH) can be prepared by processes known from the literature fromcarboxylic acid halides of the formula XII where Hal is halogen, inparticular from carboxylic acid chlorides.

The oximes of the formula XIII can be converted into4,5-dihydroisoxazol-3-yl derivatives (IIIγ where X═O, Y═CR¹³R¹⁴) in amanner known per se via the hydroxamic acid chlorides XIV asintermediates. From the latter, nitrile oxides are prepared in situ, andthese nitrile oxides react with alkenes to give the desired products(cf., for example, Chem. Ber. 106 (1973), 3258-3274). 1,3-Dipolarcycloaddition reactions of chlorosulfonyl isocyanate with nitrile oxidesyield 1,2,4-oxadiazolin-5-on-3-yl derivatives (IIIγ where X═O, Y═NH)(cf., for example, Heterocycles 27 (1988), 683-685).

The aldehydes of the formula XIV can be converted into2,4-dihydro-1,2,4-triazol-3-on-5-yl derivatives (IIIγ where X═NR⁹,X═NR¹²) via the semicarbazones as intermediates (cf., for example, J.Heterocyclic Chem. 23 (1986), 881-883).

2-Imidazolinyl derivatives (IIIγ where X═CR¹⁰OR¹¹, Y═NH) can also beprepared from benzonitriles of the formula XV using known methods (cf.,for example, J. Org. Chem. 52 (1987), 1017-1021).\

1,3-Dipolar cycloaddition reactions of diazoalkanes or nitriloimineswith arylalkenes of the formula XVI can be used for synthesizing3-pyrazolinyl derivatives (IIIγ where X═NH, Y═CHR¹³)

The bromine- or iodine-substituted compounds of the formula V which areused as starting compounds can be obtained from corresponding anilinesby method similar to those known from the literature, for example bySandmeyer reaction, and the anilines, in turn, are synthesized byreducing suitable nitro compounds. The bromine-substituted compounds ofthe formula V can additionally be obtained by direct bromination ofsuitable starting materials (cf. Monatsh. Chem. 99 (1968), 815-822).

The nitriles of the formula VI can be obtained as described above.Equally, it is possible to synthesize them from corresponding anilinesby means of a Sandmeyer reaction.

The starting compounds of the formula VII are known (cf., for example,Coll. Czech. Chem. Commun. 40 (1975), 3009-3019) or can be preparedreadily by a suitable combination of known syntheses.

For example, the sulfonates VII (L⁴=OSO₂CF₃, OSO₂F) can be obtained fromthe corresponding phenols, which, in turn, are known (cf., for example,EP-A 195 247) or can be prepared by known methods (cf., for example,Synthesis 1993, 735-762).

The halogen compounds VII (L⁴=Cl, Br or I) can be obtained, for example,from the corresponding anilines of the formula XIX by a Sandmeyerreaction.

The amidoximes of the formula IX, the thioamides of the formula X andthe carboxylic acids of the formula XI can be synthesized from thenitriles of the formula XV in a manner known per se.

Furthermore, it is possible to prepare the carboxylic acids of theformula XI from the aldehydes of the formula XIV by known processes(cf., for example, J. March, Advanced Organic Chemistry, 3rd edition(1985), p. 629 et seq., Wiley-Interscience Publication).

The carboxylic acid halides of the formula XII can be obtained from thecorresponding carboxylic acids of the formula XI by methods similar tostandard processes.

The oximes of the formula XIII are advantageously obtained by reactingaldehydes of the formula XIV with hydroxylamine in a manner known per se(cf., for example, J. March, Advanced Organic Chemistry, 3rd ed. (1985),pp. 805-806, Wiley-Interscience Publication).

Those aldehydes of the formula XIV which are not already known can beprepared by methods similar to known processes. Thus, they can besynthesized from methyl compounds of the formula XVII by means ofbromination, for example with N-bromosuccinimide or1,3-dibromo-5,5-dimethylhydantoin, followed by oxidation (cf. Synth.Commun. 22 (1992), 1967-1971).

The oximes of the formula XIII can also be converted into nitrites ofthe formula XV by processes which are-known per se (cf., for example, J.March, Advanced Organic Chemistry, 3rd ed. (1985), pp. 931-932,Wiley-Interscience Publication).

Arylalkenes of the formula XVI can be synthesized starting from thehalogen compounds or sulfonates of the formula VII (L⁴=Br, Cl, OSO₂CF₃,OSO₂F) by, inter alia, Heck reaction with olefins in the presence of apalladium catalyst (cf., for example, Heck, Palladium Reagents inOrganic Synthesis, Academic Press, London 1985; Synthesis 1993,735-762).

PREPARATION EXAMPLES4-[2-Chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-benzoyl]-5-hydroxy-1-methyl-1H-pyrazole(compound 3.35)

43.60 g (0.13 mol) of2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl chloridein 375 ml of anhydrous dioxane and 13.56 g (0.134 mol) of triethylaminein 375 ml of anhydrous dioxane are simultanouesly added dropwise at roomtemperature under a protective gas atmosphere to a solution 12.74 g(0.13 mol) of 5-hydroxy-1-methylpyrazole and 300 ml of anhydrousdioxane. After the reaction mixture had been stirred for 2 hours at roomtemperature, it was filtered through silica gel and the residue waswashed with dioxane. The eluate was concentrated in vacuo toapproximately 500 ml, and 17.94 by(0.13 mol) of dried, finely powderedpotassium carbonate were added. After the mixture had been refluxed for6 hours, the solvent was distilled off in vacuo and the residue wastaken up in approximately 700 ml of water. Insoluble constituents werefiltered off, and the pH of the filtrate was brought to 2-3 by slowaddition of 10% strength hydrochloric acid. The precipitate which formedwas filtered off with suction. This gave 46.16 g (92% of theory) of4-[2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-5-hydroxy-1-methyl-1H-pyrazole.

(m.p.>250° C.)

Table 3 shows the above compound and, in addition, other3-heterocyclyl-substituted benzoyl derivatives of the formula I whichwere prepared, or can be prepared, in a similar manner (if the endproducts had not precipitated upon acidification with 10% strengthhydrochloric acid, they were extracted with ethyl acetate ordichloromethane; the organic phase was subsequently dried andconcentrated in vacuo): TABLE 3 I

Physical data m.p. [° C.]; ¹H NMR [δ No. R¹ R² R³ X R⁴ R⁵ Y R¹⁶ Z R¹⁸ inppm] 3.1 Cl Cl H O H H CH₂ n-C₄H₉ H H 116-117 3.2 Cl Cl H O H H CH₂i-C₄H₉ H H 148-151 3.3 Cl Cl H O H H CH₂ n-C₄H₉ C₂H₅SO₂ H 0.95(t);1.32(m); 1.62(t); 1.92(quin); 3.30(t); 3.78(quar) 4.17(t); 4.61(t);7.42(d); 7.48(m). 3.4 Cl Cl H O H H CH₂ i-C₄H₉ i-C₄H₉SO₂ H 0.96(d);1.21(d); 2.33(m); 2.48(m); 3.30(t); 3.67(d); 3.97(d); 4.58(t); 7.42(d);7.50(m). 3.5 Cl Cl H O H H CH₂ n-C₃H₇ i-C₄H₉SO₂ H 0.97(t); 1.20(d);1.96(m); 2.49(m); 3.30(t); 3.68(d); 4.12(t); 4.59(t); 7.42(d); 7.49(d);7.52(s). 3.6 Cl Cl H O H H CH₂ n-C₃H₇ C₂H₅SO₂ H 0.97(t),1.12(d);1.63(t); 1.94(m); 3.29(t); 3.76(q); 4.14(t); 4.60(t); 7.42(d),7.48(d);7.51(s). 3.7 Cl SO₂CH₃ H O COOC₂H₅ H CH₂ CH₃ H H 70-75 3.8 Cl SO₂CH₃ H OCOOC₂H₅ H CH₂ C₂H₅ H H 65-70 3.9 Cl SO₂CH₃ H O CH₃ H CH₂ CH₃ H H 230-2353.10 Cl SO₂CH₃ H O CH₃ H CH₂ C₂H₅ H H 210-215 3.11 Cl SO₂CH₃ H O CH₃ HCH₂ n-C₃H₇ H H  95-100 3.12 Cl SO₂CH₃ H O CH₃ H CH₂ CH₃ C₂H₅SO₂ H 70-753.13 Cl SO₂CH₃ H O CH₃ H CH₂ C₂H₅ C₂H₅SO₂ H 78-83 3.14 Cl SO₂CH₃ H O CH₃H CH₂ C₂H₅ i-C₄H₉SO₂ H 1.24(2d); 1.53(t); 2.52(m); 3.05(dd); 3.29(s);3.52(dd); 3.73(d); 4.24(q), 5.05(m); 7.49(s); 7.66(d); 8.18(d). 3.15 ClSO₂CH₃ H O CH₃ H CH₂ n-C₃H₇ C₂H₅SO₂ H 0.96(t); 1.53(d); 1.68(t);1.95(sext); 3.07(dd); 3.32(s); 3.58(dd); 3.86(quart); 4.15(t); 5.03(m);7.46(d); 7.64(d); 8.18(d). 3.16 Cl SO₂CH₃ H O CH₃ CH₃ CH₂ CH₃ H H220-225 3.17 Cl SO₂CH₃ H O CH₃ CH₃ CH₂ C₂H₅ H H 82-86 3.18 Cl SO₂CH₃ H OCH₃ CH₃ CH₂ n-C₃H₇ H H 70-75 3.19 Cl SO₂CH₃ H O CH₃ CH₃ CH₂ n-C₄H₉ H H68-73 3.20 Cl SO₂CH₃ H O CH₃ CH₃ CH₂ i-C₄H₉ H H 45-50 3.21 Cl SO₂CH₃ H OC₂H₅ H CH₂ CH₃ H H 220-225 3.22 Cl SO₂CH₃ H O C₂H₅ H CH₂ C₂H₅ H H170-175 3.23 Cl SO₂CH₃ H O H H CH₂ n-C₃H₇ H H 65-70 3.24 Cl SO₂CH₃ H O HH CH₂ n-C₄H₉ H H 55-60 3.25 Cl SO₂CH₃ H O H H CH₂ i-C₄H₉ H H 58-63 3.26Cl SO₂CH₃ H O H H CH₂ n-C₄H₉ C₂H₅SO₂ H 78-83 3.27 Cl SO₂CH₃ H O H H CH₂n-C₄H₉ i-C₄H₉SO₂ H 0.94(t); 1.19(d); 1.22(t); 1.38(m); 1.74(br);1.91(m); 2.53(m); 3.26(s); 4.45(t); 3.76(d); 4.18(t); 4.62(t); 7.45(s);7.64(d); 8.16(d). 3.28 Cl SO₂CH₃ H O H H CH₂ i-C₄H₉ i-C₄H₉SO₂ H 0.96(d);1.21(d); 2.33(m); 2.51(m); 3.75(d); 3.99(d); 4.61(t); 7.45(s); 7.66(d);8.17(d). 3.29 Cl SO₂CH₃ H O H H CH₂ i-C₄H₉ C₂H₅SO₂ H 0.97(d); 1.66(t);2.36(m); 3.29(s); 3.43(t); 3.82(q); 3.99(d); 4.60(t); 7.47(s); 7.68(d);8.18(d). 3.30 Cl SO₂CH₃ H O H H CH₂ CH₃ C₂H₅SO₂ H 1.68(t); 3.29(s);3.43(t); 3.78(q); 3.92(s); 3.63(t); 7.46(s); 7.62(d); 8.17(d). 3.31 ClSO₂CH₃ H O H H CH₂ CH₃ i-C₄H₉SO₂ H 1.23(d); 2.53(m), 3.28(s); 3.43(t);3.70(d); 3.91(s); 4.61(t); 7.48(s); 7.66(d); 8.18(d). 3.32 Cl Cl H O H HCH₂ n-C₃H₇ H H 119-121 3.33 Cl Cl H O H H CH₂ CH₃ H CH₃ 115-117 3.34 ClNO₂ H O H H CH₂ C₂H₅ H H 217-218 3.35 Cl SO₂CH₃ H O H H CH₂ CH₃ H H >2503.36 Cl Cl H O H H CH₂ C₂H₅ H H 125-128 3.37 Cl SO₂CH₃ H O H H CH₂ C₂H₅n-C₃H₇SO₂ H 78-83 3.38 Cl SO₂CH₃ H O H H CH₂ C₂H₅ C₂H₅SO₂ H 1.52(t);1.68(t); 3.29(s); 3.43(t); 3.82(q); 4.24(q); 4.63(t); 7.48(s); 7.65(d);8.07(d). 3.39 Cl SO₂C₂H₅ H O CH₃ CH₃ CH₂ CH₃ H H >200 3.40 Cl SO₂C₂H₅ HO CH₃ H CH₂ CH₃ H H 220-223 3.41 Cl SO₂C₂H₅ H O CH₃ H CH₂ C₂H₅ H H >2303.42 Cl SO₂-n-C₃H₇ H O CH₃ H CH₂ CH₃ H H 1.12(t); 1.53(d); 1.76(quin);3.18(dd); 3.38(t); 3.55(dd); 3.73(s); 5.04(m); 5.55(s, br.); 7.37(s);7.68(d); 8.13(d). 3.43 Cl SO₂-n-C₃H₇ H O CH₃ H CH₂ C₂H₅ H H 1.07(t);1.50(m); 1.78(quin) 3.07(dd); 3.39(t); 3.55(dd); 4.12(t); 5.08(m);7.38(s); 7.69(d); 8.11(d). 3.44 Cl SO₂CH₃ H CH₂ H H O CH₃ H H 3.45^(a))Cl SO₂CH₃ H C(CH₃)₂ H H O CH₃ H H 1.33(s); 3.40(s); 4.17(s); 7.43(s);7.79(d); 8.04(d). 3.46 Cl SO₂CH₃ H O H H CH₂ C₂H₅ Na⁺ H 218-220 3.47 ClSO₂CH₃ H O H H CH₂ C₂H₅ K⁺ H 193 3.48 Cl SO₂CH₃ H O H H CH₂ C₂H₅ Li⁺H >230 3.49 Cl SO₂CH₃ H O H H CH₂ C₂H₅ NH₄ ⁺ H 170-175 3.50 Cl SO₂CH₃ HO H H CH₂ CH₃ Na⁺ H >240 3.51 Cl SO₂CH₃ H O H H CH₂ CH₃ K⁺ H 206-2143.52 Cl SO₂CH₃ H O H H CH₂ CH₃ Li⁺ H >240 3.53 Cl SO₂CH₃ H O H H CH₂ CH₃NH₄ ⁺ H 3.54^(a)) Cl SO₂CH₃ H C(CH₃)₂ H H O C₂H₅ H H 1.27(t); 1.36(s);3.41(q); 4.01(q); 4.18(s); 7.47(s); 7.83(d); 8.07(d). 3.55 Cl SO₂CH₃ H OH —(CH₂)₃CH— C₂H₅ H H  99-104 3.56 Cl SO₂CH₃ H O H —(CH₂)₃CH— CH₃ H H 95-100 3.57 Cl SO₂CH₃ H O —(CH₂)₄— CH₂ CH₃ H H 230-235 3.58 Cl SO₂CH₃ HO —(CH₂)₄— CH₂ C₂H₅ H H 190-195 3.59 Cl SO₂CH₃ H O —(CH₂)₂O(CH₂)₂— CH₂C₂H₅ H H  95-100 3.60 Cl SO₂C₂H₅ H O CH₃ CH₃ CH₂ CH₃ H H <230 3.61 ClSO₂C₂H₅ H O CH₃ CH₃ CH₂ C₂H₅ H H 198-200 3.62 Cl SO₂C₂H₅ H O H H CH₂ CH₃H H 215-218 3.63 Cl SO₂C₂H₅ H O H H CH₂ C₂H₅ H H 213-215 3.64 ClSO₂-n-C₃H₇ H O H H CH₂ CH₃ H H 186-190 3.65 Cl SO₂-n-C₃H₇ H O H H CH₂C₂H₅ H H 84-86 3.66 Cl SO₂CH₃ H O —(CH₂)₂O(CH₂)₂— CH₂ CH₃ H H 90-95 3.67Cl SO₂CH₃ H O C₂H₅ C₂H₅ CH₂ CH₃ H H 70-75 3.68 Cl SO₂CH₃ H O C₂H₅ C₂H₅CH₂ C₂H₅ H H 50-55 3.69 Cl SO₂CH₃ H O OCH₃ H CH₂ CH₃ H H 3.18-3.99(11H);5.78(1H); 7.50(1H); 7.81(1H); 8.09(1H). 3.70 Cl SO₂CH₃ H O CH₃ H CHCH₂ClCH₃ H H 1.52(3H); 3.30- 4.12(8H); 4.36(1H); 4.93(1H); 7.49(1H);7.81(1H); 8.09(1H). 3.71 Cl SO₂CH₃ H O CH₃ H CHCH₂Cl C₂H₅ H H 1.27(3H);1.55(3H); 3.28-4.02(7H) 4.37(1H); 4.92(1H); 7.48(1H); 7.80(1H); 8.07(1H)3.72 Cl SO₂CH₃ H C(CH₃)₂ H H O CH₃ H H 132-135 3.73 Cl SO₂CH₃ H O C₂H₅ HCH₂ CH₃ H H  95-100 3.74 Cl SO₂CH₃ H O C₂H₅ H CH₂ C₂H₅ H H 1.16(3H);1.27(3H); 3.20-4.00(9H); 5.89(1H); 7.50(1H); 7.82(1H); 8.07(1H). 3.75 ClSO₂CH₃ H O C₂H₅ C₂H₅ CH₂ C₂H₅ K⁺ H 200-205 3.76 Cl SO₂C₂H₅ H C(CH₃)₂ H HO CH₃ H H 120-123 3.77 Cl SO₂-n-C₃H₇ H O CH₃ CH₃ CH₂ C₂H₅ H H 152-1583.78 Cl SO₂-n-C₃H₇ H O CH₃ CH₃ CH₂ CH₃ H H 172-176 3.79 Cl SO₂-n-C₃H₇ HO CH₃ H CH₂ CH₃ H H 188-205 3.80 Cl SCH₃ H O H H CH₂ C₂H₅ H H 1.29(t);2.56(s); 3.28(t); 3.93(q); 4.49(t); 7.40(s); 7.43(d); 7.55(d). 3.81 ClSO₂CH₃ H O CH₂Cl H CH₂ C₂H₅ H H 78-82 3.82 CH₃ H H CH₂ H H S C₂H₅ H H1.44(t); 2.50(s); 3.49(t); 4.09(q); 4.53(t); 7.35(m); 7.48(d); 7.62(d).3.83 Cl SO₂CH₃ H O CH₂Cl H CH₂ CH₃ H H 81-85 3.84 Cl SCH₃ H O H H CH₂CH₃ H H 151-153 3.85 Cl SOCH₃ H O H H CH₂ C₂H₅ H H 1.28(t); 2.82(s);3.40(m); 3.92(m); 4.52(t); 7.45(s); 7.82(d); 8.10(d). 3.86 CH₃ SO₂CH₃ HO H H CH₂ CH₃ H H 205-210 3.87 Cl Cl H CH₂ H H S C₂H₅ H H 173-179 3.88Cl SCH₃ H CH₂ H H S C₂H₅ H H 1.43(t); 2.51(s); 3.59(t); 4.08(q);4.51(t); 7.22(d); 7.41(s); 7.50(d). 3.89 Cl SO₂CH₃ H CH₂ H H S C₂H₅ H H1.50(t); 3.28(s); 3.62(t); 4.10(q); 4.49(t); 7.36(s); 7.68(d); 8.19(d).3.90 CH₃ SO₂CH₃ H O H H CH₂ C₂H₅ H H 174-180 3.91 Cl SO₂CH₃ H O CH₂Cl HCH₂ CH₃ H H 77-83 3.92 Cl SO₂CH₃ H O F H CH₂ CH₃ H H 3.93 Cl SO₂CH₃ H OF H CH₂ C₂H₅ H H 3.94 Cl SO₂CH₃ H O F F CH₂ CH₃ H H 3.95 Cl SO₂CH₃ H O FF CH₂ C₂H₅ H H 3.96 Cl SO₂CH₃ H O CH₃ H CHCH₃ C₂H₅ H H 183-184 3.97 ClSO₂CH₃ H O CF3 H CH₂ CH₃ H H 223-225 3.98 Cl SO₂CH₃ H O CF3 H CH₂ C₂H₅ HH 183-184 3.99 Cl SO₂CH₃ H O SC₂H₅ H CH₂ CH₃ H H 195-196 3.100 Cl SO₂CH₃H O SC₂H₅ H CH₂ C₂H₅ H H 199-200 3.101 Cl SO₂CH₃ H O CH₃ H CHCH₃ CH₃ H H230-233 3.102 Cl SO₂CH₃ H O CHCl(CH₃) H CH₂ C₂H₅ H H 102-107 3.103 ClSO₂CH₃ H O CHCl(CH₃) H CH₂ CH₃ H H 80-85 3.104 Cl SO₂CH₃ H O n-C₃H₇ HCH₂ CH₃ H H 3.105 Cl SO₂CH₃ H O n-C₃H₇ H CH₂ C₂H₅ H H 3.106 Cl SO₂CH₃ HO H H CH₂ CH₃ ⁺NH₂(CH₃)₂ H 200 3.107 Cl SO₂CH₃ H O H H CH₂ CH₃⁺NH₂(CH₂CH₂OH) H 187 3.108 Cl SO₂CH₃ H O H H CH₂ CH₃ ⁺NH₃(CH₂CH₂OCH₂ H180 CH₂OH) 3.109 SCH₃ SCH₃ H O H H CH₂ CH₃ H H 2.33(s); 2.51(s);3.40(t); 3.70(s); 4.58(t); 5.15(brs); 7.21(s); 7.31(d); 7.42(d) 3.110SCH₃ SCH₃ H O H H CH₂ C₂H₅ H H 1.38(t); 2.33(s); 2.49(s); 3.41(t);4.10(q); 4.58(t); 7.25(s); 7.32(d); 7.41(d); 7.82(brs). 3.111 SO₂CH₃SO₂CH₃ H O H H CH₂ CH₃ H H oil 3.112 SO₂CH₃ SO₂CH₃ H O H H CH₂ C₂H₅ H Hoil^(a))Prepared from2-chloro-3-(1′-chloro-2′,2′-dimethylethylaminocarbonyl)-4-methylsulfonylbenzoylchloride with two equivalents of potassium carbonate.

The syntheses of some starting materials are given below:

2-Chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl chloride(compound 4.5) Step a) 2-Chloro-3-methyl-4-methylthioacetophenone

A solution of 157 g (2 mol) of acetyl chloride in 420 mol of1,2-dichlorethane was added dropwise to a suspension of 286 g (2.14 mol)of aluminum trichloride in 420 ml of 1,2-dichloroethane at 15-20° C. Asolution of 346 g (2 mol) of 2-chloro-6-methylthiotoluene in 1 1 of1,2-dichlorethane was subsequently added dropwise. After the reactionmixture had been stirred for 12 hours, it was poured into a mixture of 31 of ice and 1 l of concentrated HCl. The mixture was extracted withmethylene chloride, and the organic phase was washed with water, driedwith sodium sulfate and concentrated. The residue was distilled invacuo. This gave 256 g (60% of theory) of2-chloro-3-methyl-4-methylthioacetophenone.

(m.p.: 46° C.)

Step b) 2-Chloro-3-methyl-4-methylsulfonylacetophenone

163.0 g (0.76 mol) of 2-chloro-3-methyl-4-methylthioacetophenone weredissolved in 1.5 l of glacial acetic acid, 18.6 g of sodium tungstatewere added, and 173.3 g of a 30% strength hydrogen peroxide solutionwere added dropwise with cooling. Stirring was continued for 2 days andthe mixture was subsequently diluted with water. The solid which hadprecipitated was filtered off with suction, washed with water and dried.This gave 164.0 g (88% of theory) of2-chloro-3-methyl-4-methylsulfonyl-acetophenone.

(m.p.: 110-111° C.)

Step c) 2-Chloro-3-methyl-4-methylsulfonylbenzoic acid

82 g (0.33 mol) of 2-chloro-3-methyl-4-methyl-sulfonylacetophenone weredissolved in 700 ml of dioxane, and 1 l of a 12.5% strength sodiumhypochlorite solution was added at room temperature. Stirring wascontinued for 1 hour at 80° C. After cooling, two phases formed, ofwhich the bottom phase was diluted with water and acidifed weakly. Thesolid which had precipitated was filtered off with suction, washed withwater and dried. This gave 60 g (73% of theory) of2-chloro-3-methyl-4-methylsulfonylbenzoic acid.

(m.p.: 230-231° C.)

Step d) Methyl 2-chloro-3-methyl-4-methylsulfonylbenzoate

100 g (0.4 mol) of 2-chloro-3-methyl-4-methyl-sulfonylbenzoic acid weredissolved in 1 l of methanol and hydrogen chloride gas was passed in for5 hours at reflux temperature. The mixture was subsequentlyconcentrated. This gave 88.5 g (84% of theory) of methyl2-chloro-3-methyl-4-methylsulfonylbenzoate.

(m.p.: 107-108° C.)

Step e) Methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate

82 g (0.1 mol) of methyl 2-chloro-3-methyl-4-methyl-sulfonylbenzoate aredissolved in 2 l of tetrachloromethane, and 56 g (0.31 mol) ofN-bromosuccinimide are added in portions with exposure to light. Thereaction mixture was filtered, the filtrate was concentrated, and theresidue was taken up in 200 ml of methyl tert-butyl ether. The solutionwas treated with petroleum ether and the solid which had precipitatedwas filtered off with suction and dried. This gave 74.5 g (70% oftheory) of methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate.

(m.p.: 74-75° C.)

Step f) Methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate

A solution of 41.0 g (0.12 mol) of methyl3-bromomethyl-2-chloro-4-methylsulfonylbenzoate in 250 ml ofacetonitrile was treated with 42.1 g (0.36 mol) of N-methylmorphlineN-oxide. The batch was stirred for 12 hours at room temperature andsubsequently concentrated, and the residue was taken up in ethylacetate. The solution was extracted with water, dried with sodiumsulfate and concentrated. This gave 31.2 g (94% of theory) of methyl2-chloro-3-formyl-4-methylsulfonylbenzoate

(m.p.: 98-105° C.)

Step g) 2-Chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoic acid

15.00 g (54 mmol) of methyl 2-chloro-3-formyl-4-methyl-sulfonylbenzoateand 4,20 g (60 mmol) of hydroxylamine hydrochloride were taken up in 300ml of methanol, and a solution of 3.18 g (30 mmol) of sodium carbonatein 80 ml of water was added dropwise. After the mixture had been stirredfor 12 hours at room temperature, the methanol was distilled off, theresidue was diluted with water and the mixture was extracted withdiethyl ether. After the organic phase had been dried, the solvent wasremoved. This gave 14.40 g (91% of theory) of methyl2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate.

(m.p.: 126-128° C.).

Step h) Methyl2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate (compound4.3)

Ethylene was passed for 30 minutes at 15-20° C. into a solution of 158.0g (0.54 mol) of methyl2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate and 1 l ofdichloromethane. After 1.6 g of sodium acetate had been added, 454 ml ofsodium hydrochlorite solution were added dropwise at 10° C. whilesimultaneously passing in ethylene. Ethylene was subsequently passed inat 10° C. for a further 15 minutes. After the mixture had been stirredfor 12 hours, the phases were separated, and the organic phase waswashed with water, dried and concentrated. This gave 156.5 g (90% oftheory) of methyl2-chloro-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate.

(¹H NMR (δ in ppm): 3.24 (s); 3.42 (t); 3.99 (s); 4.60 (t);

7.96 (d); 8.10 (d)).

Step i) 2-Chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-benzoicacid (compound 4.4)

A solution of 32.8 g of sodium hydroxide, dissolved in 330 ml ofmethanol, was slowly added dropwise to a mixture of 170.0 g (0.54 mol)of methyl 2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoateand 1 l of methanol at 40-45° C. The suspension was stirred for 5 hoursat 50° C. After the solvent had been distilled off, the residue wastaken up in 1.5 l of water, and the aqueous phase was extracted threetimes with ethyl acetate. The aqueous phase was acidified withhydrochloric acid and extracted three times with ethyl acetate. Thecombined organic phases were subsequently washed to neutrality withwater, dried and concentrated. This gave 148.8 g (91% of theory) of2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-benzoic acid.

(¹H NMR (δ in ppm): 3.26 (s); 3.45 (t); 4.63 (t); 8.15 (s) 8.53 (s,br)).

Step j) 2-Chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-benzoylchloride (compound 4.5)

74.8 g (0.63 mol) of thionyl chloride in 50 ml of dry toluene were addeddropwise at 50° C. to a solution of 139.0 g of2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid, 1 mlof dimethylformamide and 1 l of dry toluene. After the mixture had beenheated for 6 hours at 110° C., the solvent was distilled off. This gave2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methyl-sulfonylbenzoyl chloridein quantitative yield.

(¹H NMR (δ in ppm): 3.25 (s); 3.46 (t); 4.62 (t); 8.21 (dd)).

2-Chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-benzoylchloride (compound 4.39) Step a) Methyl2-chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate(compound 4.25)

Propene was passed for 30 minutes at room temperature into a solution of15.0 g (52 mmol) of methyl2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate and 200 ml ofdichloromethane. After 1.6 g of sodium acetate had been added, 42.8 mlof sodium hydrochlorite [sic] solution were added dropwise at roomtemperature while simultaneously passing in propene. Propene wassubsequently passed in for a further 15 minutes at room temperature.After the mixture had been refluxed for 3 hours, it was stirred for 12hours at room temperature, propene was again passed in for 5 hours underreflux, and the mixture was stirred for a further 12 hours at roomtemperature. After the phases had been separated, the organic phase waswashed with water, dried and concentrated. This gave 15.5 g (89% oftheory) of methyl2-chloro-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methyl-sulfonylbenzoate.

(m.p.: 130-135° C.)

Step b)2-Chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methyl-sulfonylbenzoicacid (compound 4.26)

A solution of 3.52 g (88 mmol) of sodium hydroxide, dissolved in 100 mlof methanol, was slowly added dropwise to a mixture of 15.00 g (45 mmol)of methyl2-chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methyl-sulfonylbenzoateand 200 ml of methanol. The suspension was stirred for 48 hours at roomtemperature. After the solvent had been distilled off, the residue wastaken up in water, and the aqueous phase was washed three times withethyl acetate. The aqueous phase was acidified with hydrochloric acidand extracted three times with ethyl acetate. The combined organicphases were subsequently washed to neutrality with water, dried andconcentrated. This gave 13.20 g (92% of theory) of2-chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoicacid.

(m.p.: 173-178° C.)

Step c)2-Chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methyl-sulfonylbenzoylchloride (compound 4.39)

5.7 g (51 mmol) of thionyl chloride were added dropwise at roomtemperature to a solution of 13.0 g (41 mmol) of2-chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methyl-sulfonylbenzoicacid, 1 ml of dimethylformamide and 250 ml of dry toluene. The mixturewas subsequently refluxed until the reaction was complete. Aftercooling, the solvent was distilled off. This gave 14.2 g of2-chloro-3-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methyl-benzoyl chloridein quantitative yield.

2-Chloro-3-(1′-chloro-2′,2′-dimethylethylaminocarbonyl)-4-methyl-sulfonylbenzoylchloride Step a) Methyl2-chloro-3-hydroxycarbonyl-4-methyl-sulfonylbenzoate

13.8 g (0.11 mol) of sodium hydrogen phosphate monohydrate in 170 ml ofwater, 49.3 g (0.43 mol) of 30% strength hydrogen peroxide solution and66.2 g (0.59 mol) of 80% strength aqueous sodium chlorite solution wereadded in succession at 5° C. to a solution of 115.3 g (0.42 mol) ofmethyl 2-chloro-3-formyl-4-methyl-sulfonylbenzoate and [sic] 2000 ml ofacetonitrile. The reaction solution was subsequently stirred for 1 hourat 5° C. and for 12 hours at room temperature. The pH was then broughtto 1 with 10% strength hydrochloric acid, and 1500 ml of aqueous 40%strength sodium hydrogen sulfite solution were added. After the mixturehad been stirred for 1 hour at room temperature, the aqueous phase wasextracted three times with ethyl acetate. The combined organic phaseswere washed with sodium hydrogen sulfite solution and dried. After thesolvent had been distilled off, 102.0 g of methyl2-chloro-3-hydroxycarbonyl-4-methylsulfonylbenzoate were obtained.

(¹H NMR (δ in ppm): 3.34 (s); 3.93 (s); 8.08 (s); 14.50 (s, br.).)

Step b) Methyl 2-chloro-3-chlorocarbonyl-4-methylsulfonylbenzoate

2 drops of dimethylformamide and 11.9 g (0.1 mol) of thionyl chloridewere added to a solution of 6.0 g (0.021 mol) of methyl2-chloro-3-hydroxycarbonyl-4-methylsulfonylbenzoate and 50 ml of drytoluene. The solution was refluxed for 4 hours. After the solvent hadbeen removed in vacuo, 6.2 g of methyl2-chloro-3-chlorocarbonyl-4-methylsulfonylbenzoate were obtained.

(¹H NMR (δ in ppm): 3.21 (s); 4.02 (s); 8.02 (d); 8.07 (d).)

Step c) Methyl2-chloro-3-(1′-hydroxy-2′,2′-dimethylethylaminocarbonyl)-4-methylsulfonylbenzoate

A solution of 7.80 g (25 mmol) of methyl2-chloro-3-chlorocarbonyl-4-methylsulfonylbenzoate was added dropwise at0-5° C. to a solution of 4.54 g (50 mmol) of 2,2-dimethylethanolamine in40 ml of dichloromethane. After the reaction solution had been stirredfor 6 hours at room temperature, it was extracted three times withwater, dried and concentrated. This gave 8.20 g (80% of theory) ofmethyl2-chloro-3-(1′-hydroxy-2′,2′-dimethylethylaminocarbonyl)-4-methylsulfonylbenzoate.

(m.p.: 70-72° C.).

Step d) Methyl2-chloro-3-(1′-chloro-2′,2′-dimethyl-ethylaminocarbonyl)-4-methylsulfonylbenzoate

A mixture of 6.9 g (20 mmol) of methyl2-chloro-3-(1′-hydroxy-2′,2′-dimethylethylamino-carbonyl)-4-methylsulfonylbenzoateand 5 ml of thionyl chloride was stirred for 6 hours at roomtemperature. The solution was diluted with 50 ml of dichloromethane andsubsequently concentrated. The residue was dissolved in 20 ml ofdichloromethane. The addition of cyclohexane resulted in a crystallineprecipitate which was filtered off with suction and dried. This gave 6.4g (88% of theory) of methyl2-chloro-3-(1′-chloro-2′,2′-dimethylethylaminocarbonyl)-4-methylsulfonylbenzoate.

Step e)2-Chloro-3-(4′,4′-dimethyl-4′,5′-dihydroxazol-2-yl)-4-methylsulfonylbenzoicacid (compound 4.38)

A solution of 5.82 g (15 mmol) of methyl2-chloro-3-(1′-chloro-2′,2′-dimethylethyl-aminocarbonyl)-4-methylsulfonylbenzoateand 0.81 g (20 mmol) of sodium hydroxide in 80 ml of methanol wasstirred for 8 hours at room temperature. After the solvent had beendistilled off, the residue was taken up in water and the mixture waswashed three times with ethyl acetate. The aqueous phase was acidifiedwith hydrochloric acid and extracted three times with ethyl acetate.After the organic phase had been dried, the solvent was removed invacuo. This gave 3.10 g (56% of theory) of2-chloro-3-(4′,4′-dimethyl-4′,5′-dihydrooxazol-2-yl)-4-methylsulfonylbenzoicacid.

(¹H NMR (δ in ppm): 1.34 (s); 3.40 (s); 4.13 (s); 8.07 (s); 13.95 (s,br)).

Step f)2-Chloro-3-(1′-chloro-2′,2′-dimethylethylaminocarbonyl)-4-methylsulfonylbenzoylchloride

A solution of 3.00 g (9 mmol) of2-chloro-3-(4′,4′-dimethyl-4′,5′-dihydrooxazol-2-yl)-4-methylsulfonyl-benzoicacid, 1.43 g of thionyl chloride and 1 drop of dimethylformamide in 80ml of dry toluene was refluxed for 3 hours. After cooling, the solventwas distilled off in vacuo. This gave 3.43 g (86% of theory) of2-chloro-3-(1′-chloro-2′,2′-dimethylethylaminocarbonyl)-4-methylsulfonylbenzoylchloride.

Methyl2-chloro-3-(1,3,4-oxathiazolin-2-on-5-yl)-4-methylsulfonylbenzoate(compound 4.22) Step a) Methyl3-aminocarbonyl-2-chloro-4-methylsulfonylbenzoate

Ammonia was passed for 2 hours into a solution of 15.0 g (48 mmol) ofmethyl 2-chloro-3-chlorocarbonyl-4-methylsulfonylbenzoate and 300 ml ofdry dioxane. The precipitate formed was filtered off with suction andthe filtrate was concentrated. This gave 15.2 g of methyl3-aminocarbonyl-2-chloro-4-methylsulfonylbenzoate in quantitative yield.

Step b) Methyl2-chloro-3-(1,3,4-oxathiazolin-2-on-5-yl)-4-methylsulfonylbenzoate

9.80 g (75 mmol) of chlorocarbonylsulfenyl chloride were added dropwiseto a solution of 4.37 g (15 mmol) of methyl3-aminocarbonyl-2-chloro-4-methylsulfonylbenzoate in 150 ml of drytoluene. After the mixture had been stirred for 48 hours under reflux,the solvent is removed in vacuo and the residue is chromatographed onsilica gel (eluent:ethyl acetate/cyclohexane=1/1). This gave 3.70 g (70%of theory) of methyl2-chloro-3-(1,3,4-oxathiazolin-2-on-5-yl)-4-methylsulfonylbenzoate.

Methyl 2-chloro-4-methylsulfonyl-3-(4,5-dihydrooxazol-3-yl)-benzoate(compound 4.41)

At room temperature, 41.8 g (0.41 mol) of triethylamine and then 31.1 g(0.10 mol) of methyl 2-chloro-3-chlorocarbonyl-4-methylsulfonylbenzoatein 150 ml of toluene were added dropwise to 26.6 g (0.13 mol) of1-amino-2-bromoethane hydrobromide in 500 ml of toluene. The mixture washeated under reflux for 5 hours and then stirred at room temperature for12 hours, another 5.0 g (0.02 mol) of 1-amino-2-bromoethane hydrobromidewere added and the mixture was heated under reflux for 7.5 hours. Thereaction mixture was allowed to cool, diluted with ethyl acetate, washedwith water, dried and concentrated. The residue was then recrystallizedfrom methyl tert-butyl ether/ethyl acetate. 14.5 g (46% of theory) ofmethyl 2-chloro-4-methyl-sulfonyl-3-(4,5-dihydrooxazol-2-yl)benzoatewere obtained.

2-Chloro-3-(5-methoxy-5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoicacid (compound 4.60) Step a) Methyl2-chloro-3-(5-methoxy-5-methyl-4,5-dihydro-isoxazol-3-yl)-4-methylsulfonylbenzoate

7.3 g (102 mmol) of 2-methoxy-1-propene, 28 ml of sodium hypochloritesolution (12.5% strength) and a spatula-tip of sodium acetate were addedsuccessively to 10.0 g (34 mmol) of methyl2-chloro-3-(hydroxyiminomethyl)-4-methylsulfonylbenzoate in 200 ml ofmethylene chloride. The mixture was stirred at room temperature for 12hours, the solvent was removed and the residue was taken up in ethylacetate, washed with water, dried and concentrated. The residue waschromatographed over silica gel (eluent: cyclohexane:ethyl acetate=3:2).This gave 5.8 g (47% of theory) of methyl2-chloro-3-(5-methoxy-5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate.(mp.: 100-105° C.)

Step b)2-Chloro-3-(5-methoxy-5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate

At reflux temperature, 5.5 g (15.0 mmol) of methyl2-chloro-3-(5-methoxy-5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoatein 100 ml of pyridine were added dropwise to 5.0 g (37.5 mmol) oflithium iodide in 200 ml of pyridine. The mixture was stirred at thistemperature for 4 hours and then cooled, the solvent was distilled offand the residue was taken up in toluene and reconcentrated. The residuewas subsequently admixed with water and washed with methylene chloride,and the pH was adjusted to 1 using hydrochloric acid. The aqueous phasewas extracted with methylene chloride and the resulting organic phasewas dried and concentrated. This gave 4.7 g (90% of theory) of2-chloro-(5-methoxy-5-methyl-4,5-di-hydroisoxazol-3-yl)-4-methylsulfonylbenzoate.(mp.: 40-45° C.)

Methyl2-chloro-3-(2-methyl-2H-1,3,4-dioxazol-5-yl)-4-methyl-sulfonylbenzoate(compound 4.44)

8.0 g (27.4 mmol) of methyl2-chloro-3-(hydroxyiminomethyl)-4-methylsulfonylbenzoate in 150 ml ofmethylene chloride were admixed dropwise with 16.0 g (27.4 mmol) of a12.5% strength sodium hypochlorite solution, and a spatula-tip of sodiumacetate was added. After 1 hour, 34.4 g (0.74 mol) of acetaldehyde wereadded a little at a time within a period of 36 hours, and the mixturewas slowly heated to 55° C. The mixture was subsequently stirred at roomtemperature for 48 hours, washed with water, dried and concentrated. Theresidue was then taken up in methylene chloride, 10.0 g (0.23 mol) ofacetaldehyde and a spatula-tip of sodium acetate were added and themixture was heated under reflux for 8 hours. After 72 hours, a further10.0 g (0.23 mol) of acetaldehyde were added and the mixture was stirredat room temperature. The mixture was subsequently washed with water,dried and concentrated. The residue was passed through silica gel(eluent: isopropanol:cyclohexane=1:9). This gave 5.0 g (55% of theory)of methyl2-chloro-3-(2-methyl-2H-1,3,4-dioxazol-5-yl)-4-methylsulfonylbenzoate.

Table 4 which follows lists the compounds which have been describedabove and also further benzoic acid derivatives of the formula III whichwere prepared, or can be prepared, by a similar method. TABLE 4 III

Physical data m.p. [° C.]; No. R¹ R² R³ X R⁴ R⁵ Y R¹⁹ ¹H NMR [δ in ppm]4.1 Cl Cl H O H H CH₂ OCH₃ 3.29(t); 3.91(s); 4.58(t); 7.46(d); 7.83(d).4.2 Cl Cl H O H H CH₂ OH 3.28(t); 4.60(t); 7.02(s, br); 7.46(d);7.98(d). 4.3 Cl SO₂CH₃ H O H H CH₂ OCH₃ 3.24(s); 3.42(t); 3.99(s);4.60(t); 7.96(d); 8.10(d). 4.4 Cl SO₂CH₃ H O H H CH₂ OH 3.26(s);3.45(t); 4.63(t); 8.15(s); 8.53(s, br). 4.5 Cl SO₂CH₃ H O H H CH₂ Cl3.25(s); 3.46(t); 4.62(t); 8.21(dd). 4.6 Cl Cl H C(CH₃)₂ H H O OH1.31(s); 4.16(s); 7.69(d); 7.90(d); 13.8(s, br). 4.7 Cl SO₂C₂H₅ H O CH₃CH₃ CH₂ OCH₃ 1.25(t); 1.57(s); 3.21(s); 3.42(q); 3.99(s); 7.94(d);8.07(d). 4.8 Cl SO₂C₂H₅ H O CH₃ CH₃ CH₂ OH 1.13(t); 1.47(s); 3.15(s);3.43(q); 8.06(s); 13.8(s, br). 4.9 Cl SO₂C₂H₅ H O H H CH₂ OCH₃ 1.28(t);3.41(m); 4.02(s); 4.62(t); 7.95(d); 8.06(d). 4.10 Cl SO₂C₂H₅ H O H H CH₂OH 137-140 4.11 Cl SO₂C₂H₅ H O CH₃ H CH₂ OCH₃ 1.26(t); 1.53(d);3.06(dd); 3.42(q); 3.49(dd); 5.05(m); 7.95(d); 8.07(d). 4.12 Cl SO₂C₂H₅H O CH₃ H CH₂ OH 140-143 4.13 Cl SO₂CH₃ H CH₂ H H O OCH₃ 3.30(s);3.98(s); 4.11(t); 4.55(t); 7.97(d); 8.08(d). 4.14 Cl SO₂CH₃ H CH₂ H H OOH 3.38(s); 4.00(t); 4.46(t); 8.08(s). 4.15 Cl SO₂CH₃ H O H H CH₂ OH3.30(s); 3.35(t); 4.15(s, br); 4.50(t); 8.05(s). 4.16 Cl SO₂-n-C₃H₇ H OCH₃ CH₃ CH₂ OCH₃ 0.95(t); 1.47(s); 1.58(quin); 3.12(s); 3.31(s);3.43(t); 3.93(s); 8.09(dd). 4.17 Cl SO₂-n-C₃H₇ H O CH₃ CH₃ CH₂ OH0.93(t); 1.47(s); 1.58(quin); 3.15(s); 3.42(t); 8.05(s). 4.18 ClSO₂-n-C₃H₇ H O H H CH₂ OCH₃ 0.92(t); 1.55(quin); 3.39(m); 3.93(s);4.50(t); 8.08(dd). 4.19 Cl SO₂-n-C₃H₇ H O H H CH₂ OH 148-150 4.20 ClSO₂-n-C₃H₇ H O CH₃ H CH₂OCH₃ 0.93 (t); 1.49(d); 1.58(quin); 2.94(dd);3.42(m); 3.93(s); 4.97(m); 8.10(dd). 4.21 Cl SO₂-n-C₃H₇ H O CH₃ H CH₂ OH0.94(t); 1.39(d); 1.58(quin); 2.96(dd); 3.50(m); 4.95(m); 8.05(s). 4.22Cl SO₂CH₃ H S ═O O OCH₃ 3.24(s); 4.02(s); 8.14(dd). 4.23 Cl SO₂CH₃ H OCOOC₂H₅ H CH₂ OCH₃ 118-121 4.24 Cl SO₂CH₃ H O COOC₂H₅ H CH₂ OH 4.25 ClSO₂CH₃ H O CH₃ H CH₂ OCH₃ 130-135 4.26 Cl SO₂CH₃ H O CH₃ H CH₂ OH173-178 4.27 Cl SO₂CH₃ H O CH₃ CH₃ CH₂ OCH₃ 1.57(s); 3.18(s); 3.27(s);4.01(s); 7.97(d); 8.12(d). 4.28 Cl SO₂CH₃ H O CH₃ CH₃ CH₂ OH 1.48(s);3.15(s); 3.34(s); 8.08(dd). 4.29 Cl SO₂CH₃ H O C₂H₅ H CH₂ OCH₃ 0.97(t);1.72(m); 3.10(dd); 3.32(s); 3.37(dd); 4.72(m); 8.08(dd). 4.30 Cl SO₂CH₃H O H —(CH₂)₃—CH— OCH₃ 1.57(m); 1.81(m); 2.21(m); 3.20(s); 4.02(s);4.32(t); 5.35(dd); 7.92(d); 8.18(d). 4.31 Cl SO₂CH₃ H O H —(CH₂)₃—CH— OH1.72(m); 2.01(m); 3.27(s); 4.24(t); 5.23(dd); 8.05(d); 8.15(d); 13.8(s,br). 4.32 Cl SO₂CH₃ H O —(CH₂)₂—O—(CH₂)₂— CH₂ OCH₃ 2.00(m); 3.23(s);3.27(s), 3.72(m); 4.00(s); 7.96(d); 8.04(d). 4.33 Cl SO₂CH₃ H O—(CH₂)₂—O—(CH₂)₂— OH 78-83 4.34 Cl SO₂CH₃ H O —(CH₂)₄— CH₂ OCH₃ 1.78(m);2.24(m); 3.27(s); 3.36(s); 3.98(s); 7.94(d); 8.12(d). 4.35 Cl SO₂CH₃ H O—(CH₂)₄— CH₂ OH 1.76(m); 2.05(m); 3.30(s); 3.33(s); 8.09(dd). 4.36 ClSO₂CH₃ H O C₂H₅ C₂H₅ CH₂ OCH₃ 1.00(t); 1.85(m); 3.13(s); 3.27(s);3.98(s); 7.94(d); 8.11(d) 4.37 Cl SO₂CH₃ H O C₂H₅ C₂H₅ CH₂ OH 0.91(t);1.76(m); 3.12(s); 3.33(s); 8.07(dd); 13.75(s, br). 4.38 Cl SO₂CH₃ HC(CH₃)₂ H H O OH 1.34(s); 3.40(s); 4.13(s); 8.07(s); 13.95(s, br). 4.39Cl SO₂CH₃ H O CH₃ H CH₂ Cl 4.40 Cl SO₂CH₃ H CH₂ H H O OH >260 4.41 ClSO₂CH₃ H CH₂ H H O OCH₃ 3.29(3H); 3.96(3H): 4.12(2H); 4.55(2H);7.98(1H); 8.09(1H). 4.42 Cl SCH₃ H O H H CH₂ OCH₃ 202-203 4.43 Cl SO₂CH₃H O COOMe H CHCO₂CH₃ OCH₃ 1.05(3H); 1.35(3H); 3.19(3H); 4.01(3H);4.09(2H); 4.35(2H); 5.06(1H); 5.77(1H); 8.08(1H); 8.17(1H). 4.44 ClSO₂CH₃ H O CH₃ H O OCH₃ 1.78(3H); 3.30(3H); 3.98(3H); 6.40(1H);8.08(1H); 8.15(1H). 4.45 Cl SO₂CH₃ H O CHO H CHCH₃ OCH₃ 80-85 4.46 ClSO₂CH₃ H O CH₃ H CHCH₂Cl OCH₃ 1.65(3H); 3.27(3H); 3.50(2H); 4.00(3H);4.22(1H); 4.88/5.08 (1H); 7.99(1H); 8.12(1H). 4.47 Cl SO₂CH₃ H O CH₃ HCHCH₂Cl OH 100-105 4.48 Cl SO₂CH₃ H O CHO H CHCH₃ OH 180-185 4.49 ClSO₂CH₃ H O SC₂H₅ H CH₂ OCH₃ 1.30(3H); 2.75(2H); 3.25(1H); 3.34(3H);3.78(1H); 3.94(3H); 6.22(1H); 8.15(2H). 4.50 Cl SO₂CH₃ H O SC₂H₅ H CH₂OH 65-67 4.51 Cl SO₂CH₃ H O CH₃ H CHCH₃ OCH₃ 1.01(3H); 1.28(3H);3.33(4H); 3.96(3H); 4.98(1H); 8.12(1H); 8.20(1H). 4.52 Cl SO₂CH₃ H O CH₃H CHCH₃ OH 68-75 4.53 Cl SO₂CH₃ H O OCOCH₃ H CH₂ OCH₃ 105-110 4.54 ClSO₂CH₃ H O H H CH₂ OH 4.55 Cl SO₂CH₃ H O OCOCH₃ H CH₂ OH 45-50 4.56 ClSO₂CH₃ H O OCH₃ H CH₂ OH 60-65 4.57 Cl SO₂CH₃ H O CHCl(CH₃) H CH₂ OCH₃1.63(3H); 3.23(3H); 3.50(2H); 3.99(3H); 4.25(1H); 4.83/5.03 (1H);7.96(1H); 8.13(1H). 4.58 Cl SO₂CH₃ H O CHCl(CH₃) H CH₂ OH 1.56(3H);3.33(3H); 3.43(2H); 4.36(1H); 4.93(1H); 8.10(2H). 4.59 Cl SO₂CH₃ H O CH₃OCH₃ CH₂ OCH₃ 100-105 4.60 Cl SO₂CH₃ H O CH₃ OCH₃ CH₂ OH 40-45 4.61 ClSO₂CH₃ H O CF₃ OCOCH₃ CH₂ OCH₃ 60-65 4.62 Cl SCH₃ H O H H CH₂ OH 4.63 ClSO2Me H O COCH₃ H CH₂ OCH₃ 2.36(3H); 3.25(3H); 3.66(2H); 4.01(3H);5.20(1H); 8.01(1H); 8.12(1H). 4.64 Cl SO₂CH₃ H O CF₃ H CH₂ OCH₃ 156 4.65Cl SO₂CH₃ H O CF₃ H CH₂ OH 170 4.66 Cl SO₂CH₃ H O F F CH₂ OCH₃ 4.67 ClSO₂CH₃ H O F F CH₂ OH 4.68 Cl SO₂CH₃ H O F H CH₂ OCH₃ 142-143 4.69 ClSO₂CH₃ H O F H CH₂ OH 4.70 Cl SO₂CH₃ H O CH₂Cl H CH₂ OCH₃ 107-110 4.71Cl SO₂CH₃ H O CH₂Cl H CH₂ OH 60-65 4.72 Cl SO₂CH₃ H O OCH₃ H CH₂ OCH₃105-110 4.73 Cl SO₂CH₃ H O OC₂H₅ H CH₂ OCH₃ 155-160 4.74 Cl SO₂CH₃ H CH₂H H S OCH₃ 4.75 CH₃ H H C═O H H S OCH₃ 112-120 4.76 Cl SO₂CH₃ H O CF₃ OHCH₂ OH 3.38(s); 3.56(d); 3.79(d); 8.16(s); 8.67(s, br). 4.77 Cl SO₂CH₃ HO O-t-C₄H₉ H CH₂ OCH₃ 130-135 4.78 Cl SO₂CH₃ H O O-t-C₄H₉ H CH₂ OH1.25(s); 3.05(dd); 3.34(s); 3.45(dd); 6.17(m); 8.08(s). 4.79 Cl SO₂CH₃ HO CH₃ H CHCH₃ OCH₃ 1.01(d); 1.28(d); 3.35(m); 3.96(s); 4.99(m); 8.12(d);8.20(d). 4.80 Cl SO₂CH₃ H O CH₃ H CHCH₃ OH 68-75 4.81 Cl SO₂CH₃ H OSC₂H₅ H CH₂ OCH₃ 1.30(t); 2.77(q); 3.25(dd); 3.34(s); 3.78(dd); 3.94(s);6.22(m), 8.24(s). 4.82 Cl SO₂CH₃ H O SC₂H₅ H CH₂ OH 65-67 4.83 SCH₃ SCH₃H O H H CH₂ OCH₂CH₃ 1.28(t); 2.30(s); 2.46(s); 3.28(t); 4.31(q);4.45(t); 7.42(d); 7.68(d). 4.84 SCH₃ SCH₃ H O H H CH₂ OH 2.32(s);2.48(s); 3.28(t); 4.42(t); 7.48(d); 7.64(d); 13.2(s). 4.85 SO₂CH₃ SO₂CH₃H O H H CH₂ OH 3.25(s); 3.35(s); 3.44(t); 8.05(d); 8.45(d).

The 3-heterocycly-substituted benzoyl derivatives of the formula I andtheir agriculturally useful salts are suitable as herbicides, both inthe form of isomer mixtures and in the form of the pure isomers. Theherbicidal compositions comprising compounds of the formula I effectvery good control of vegetation on non-crop areas, especially at highrates of application. In crops such as wheat, rice, maize, soybeans andcotton they act against broad-leaved weeds and grass weeds withoutdamaging the crop plants substantially. This effect is observedespecially at low rates of application.

Depending on the application method in question, the compounds of theformula I, or herbicidal compositions comprising them, can additionallybe employed in a further number of crop plants for eliminatingundesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napusvar. napus, Brassica napus var. napobrassica, Brassica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare,Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus spec., Manihotesculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica),Olea europaea, Oryza sativa Phaseolus lunatus, Phaseolus vulgaris, Piceaabies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyruscommunis, Ribes sylvestre, Ricinus communis, Saccharum officinarum,Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare),Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum,Vicia faba, Vitis vinifera and Zea mays.

Moreover, the compounds of the formula I can also be used in crops whichtolerate the action of herbicides due to breeding including geneticengineering methods.

The compounds of the formula I, or the herbicidal compositionscomprising them, can be employed, for example, in the form of directlysprayable aqueous solutions, powders, suspensions, alsohighly-concentrated aqueous, oily or other suspensions or dispersions,emulsions, oil dispersions, pastes, dusts, materials for spreading orgranules, by means of spraying, atomizing, dusting, spreading orpouring. The use forms depend on the intended purposes; in any case,they should guarantee the finest possible distribution of the activeingredients according to the invention.

The herbicidal compositions comprise a herbicidally active amount of atleast one compound of the formula I or of an agriculturally useful saltof I and auxiliaries conventionally used for the formulation of cropprotection products.

Suitable inert auxiliaries are essentially:

mineral oil fractions of medium to high boiling point such as keroseneand diesel oil, furthermore coal tar oils and oils of vegetable oranimal origin, aliphatic, cyclic and aromatic hydrocarbons, eg.paraffins, tetrahydronaphthalene, alkylated naphthalenes and theirderivatives, alkylated benzenes and their derivatives, alcohols such asmethanol, ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone, strongly polar solvents, eg. amines such asN-methylpyrrolidone and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thesubstrates [sic], as such or dissolved in an oil or solvent, can behomogenized in water by means of wetting agent, tackifier, dispersant oremulsifier. However, it is also possible to prepare concentratescomposed of active substance, wetting agent, tackifier, dispersant oremulsifier and, if appropriate, solvent or oil, and these concentratesare suitable for dilution with water.

Suitable surfactants (adjuvants) are the alkali metal, alkaline earthmetal and ammonium salts of aromatic sulfonic acids, eg. ligno-,phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fattyacids, of alkyl- and alkylaryl sulfonates, of alkyl sulfates, laurylether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-,hepta- and octadecanols, and of fatty alcohol glycol ether, condensatesof sulfonated naphthalene and its derivatives with formaldehyde,condensates of naphthalene, or of the naphthalenesulfonic acids, withphenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylatedisooctyl-, octyl- or nonylphenol, alkylphenyl, tributylphenyl polyglycolether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcoholethylene oxide condensates, ethoxylated castor oil, polyoxyethylenealkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycolether acetate, sorbitol esters, lignin-sulfite waste liquors ormethylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing orconcomitantly grinding the active substances with a solid carrier.

Granules, eg. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active ingredients to solidcarriers. Solid carriers are mineral earths such as silicas, silicagels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic material, fertilizers such as ammoniumsulfate, ammonium phosphate, ammonium nitrate, ureas and products ofvegetable origin such as cereal meal, tree bark meal, wood meal andnutshell meal, cellulose powders or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-useproducts can be varied within wide ranges. In general, the formulationscomprise approximately from 0.001 to 98% by weight. preferably 0.01 to95% by weight, of at least one active ingredient. The active ingredientsare employed in a purity of from 90% to 100%, preferably 95% to 100%(according to NMR spectrum).

The formulation examples below illustrate the preparation of suchproducts:

-   -   I. 20 parts by weight of the compound No. 3.2 are dissolved in a        mixture composed of 80 parts by weight of alkylated benzene, 10        parts by weight of the adduct of 8 to 10 mol of ethylene oxide        and 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of        calcium dodecylbenzenesulfonate and 5 parts by weight of the        adduct of 40 mol of ethylene oxide and 1 mol of castor oil.        Pouring the solution into 100,000 parts by weight of water and        finely distributing it therein gives an aqueous dispersion which        comprises 0.02% by weight of the active ingredient.    -   II. 20 parts by weight of the compound No. 3.9 are dissolved in        a mixture composed of 40 parts by weight of cyclohexanone, 30        parts-by weight of isobutanol, 20 parts by weight of the adduct        of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10        parts by weight of the adduct of 40 mol of ethylene oxide and 1        mol of castor oil. Pouring the solution into 100,000 parts by        weight of water and finely distributing it therein gives an        aqueous dispersion which comprises 0.02% by weight of the active        ingredient.    -   III. 20 parts by weight of the active ingredient No. 3.10 are        dissolved in a mixture composed of 25 parts by weight of        cyclohexanone, 65 parts by weight of a mineral oil fraction of        boiling point 210 to 280° C. and 10 parts by weight of the        adduct of 40 mol of ethylene oxide and 1 mol of castor oil.        Pouring the solution into 100,000 parts by weight of water and        finely distributing it therein gives an aqueous dispersion which        comprises 0.02% by weight of the active ingredient.    -   IV. 20 parts by weight of the active ingredient No. 3.16 are        mixed thoroughly with 3 parts by weight of sodium        diisobutylnaphthalenesulfonate, 17 parts by weight of the sodium        salt of a lignosulfonic acid from a sulfite waste liquor and 60        parts by weight of pulverulent silica gel and the mixture is        ground in a hammer mill. Finely distributing the mixture in        20,000 parts by weight of water gives a spray mixture which        compries 0.1% by weight of the active ingredient.    -   V. 3 parts by weight of the active ingredient No. 3.21 are mixed        with 97 parts by weight of finely divided kaolin. This gives a        dust which comprises 3% by weight of the active ingredient.    -   VI. 20 parts by weight of the active ingredient No. 3.22 are        mixed intimately with 2 parts by weight of calcium        dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol        polyglycol ether, 2 parts by weight of the sodium salt of a        phenol/urea/formaldehyde condensate and 68 parts by weight of a        paraffinic mineral oil. This gives a stable oily dispersion.    -   VII. 1 part by weight of the active ingredient No. 3.34 is        dissolved in a mixture composed of 70 parts by weight of        cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol        and 10 parts by weight of ethoxylated castor oil. This gives a        stable emulsion concentrate.    -   VIII. 1 part by weight of active ingredient No. 3.35 is        dissolved in a mixture composed of 80 parts by weight of        cyclohexanone and 20 parts by weight of Wettol® EM 31 (=nonionic        emulsifier based on ethoxylated castor oil). This gives a stable        emulsion concentrate.

The compounds of the formula I, or the herbicidal compositionscomprising them, can be applied pre- or post-emergence. If the activeingredients are less well tolerated by certain crop plants, applicationtechniques may be used in which the herbicidal compositions are sprayed,with the aid of the spray apparatus, in such a way that they come intoas little contact as possible, if any, with the leaves of the sensitivecrop plants while reaching the leaves of undesirable plants which growunderneath, or the bare soil (post-directed, lay-by).

Depending on the intended aim of the control measures, the season, thetarget plants and the growth stage, the application rates of thecompound of the formula I are from 0.001 to 3.0, preferably 0.01 to 1.0kg/ha of active substanz (a.s.).

To widen the spectrum of action and to achieve synergistic effects, the3-heterocyclyl-substituted benzoyl derivatives of the formula I can bemixed and applied jointly with a large number of representatives ofother groups of herbicidally or growth-regulatory active ingredients.Suitable components in mixtures are, for example, 1,2,4-thiadiazoles,1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives,aminotriazoles, anilides, aryloxy-/hetaryloxyalkanic acids and theirderivatives, benzoic acid and its derivatives, benzothiadiazinones,2-(hetaroyl/aroyl)-1,3-cyclohexandiones, hetaryl aryl ketones,benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates,quinolinecarboxylic acid and its derivatives, chloroacetanilides,cyclohexenone oxime ether derivatives, diazines, dichloropropionic acidand its derivatives, dihydrobenzofuranes, dihydrofuran-3-ones,dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls,halocarboxylic acids and their derivatives, ureas, 3-phenyluracils,imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides,oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionicesters, phenylacetic acid and its derivatives, 2-phenylpropionic acidand its derivatives, pyrazoles, phenylpyrazoles, pyridazines,pyridinecarboxylic acid and its derivatives, pyrimidyl ethers,sulfonamides, sulfonylureas, triazines, triazinones, triazolinones,triazolcarboxamides and uracils.

Moreover, it may be advantageous to apply the compounds of the formulaI, alone or in combination with other herbicides, in the form of amixture with additional other crop protection agents, for example withpesticides or agents for controlling phytopathogenic fungi or bacteria.Also of interest is the miscibility with mineral salt solutions whichare employed for treating nutritional and trace element deficiencies.Non-phytotoxic oils and oil concentrates can also be added.

USE EXAMPLES

The herbicidal action of 3-heterocyclyl-substituted benzoyl derivativesof the formula I was demonstrated by the following greenhouseexperiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, suspended oremulsified in water, were applied directly after sowing by means offinely distributing nozzles. The containers were irrigated gently topromote germination and growth and subsequently covered with transparentplastic hoods until the plants had rooted. This cover causes [sic]uniform germination of the test plants unless this was adverselyaffected by the active ingredients.

For the post-emergence treatment, the test plants were grown to a plantheight of from 3 to 15 cm, depending on the plant habit, and only thentreated with the active ingredients which had been suspended oremulsified in water. To this end, the test plants were either sowndirectly and grown in the same containers, or they were first grownseparately as seedlings and transplanted into the test containers a fewdays prior to treatment. The rate of application for the post-emergencetreatment was 31.2 or 15.6 g/ha a.s. (active substance).

Depending on the species, the plants were kept at from 10 to 25° C. and20 to 35° C., respectively. The test period extended over 2 to 4 weeks.During this time, the plants were tended, and their response to theindividual treatments was evaluated.

Evaluation was carried out using a scale of from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialparts, and 0 means no damage or normal course of growth.

The plants used in the greenhouse experiments belonged to the followingspecies: Scientific name Common name Chenopodium album lambsquarters(goosefoot) Setaria faberii giant foxtail Sinapsis alba white mustardSolanum nigrum black nightshade Triticum aestivum winter wheat Zea maysIndian corn

Compound 3.33 (Table 3) was very effective against the abovementionedmono- and dicotyledonous harmful plants and was well tolerated in winterwheat and maize when applied post-emergence at rates of application of31.2 and 15.6 g/ha, respectively.

1. A 3-heterocyclyl-substituted benzoic acid compound of formula III,

wherein: R¹⁹ is hydroxyl or a radical which can be removed byhydrolysis, R¹ is C₁-C₂-alkyl, methoxy or methylsulfonyl; R² is nitro,halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl or C₁-C₆-haloalkylsulfonyl; R³is hydrogen, halogen or C₁-C₆-alkyl; R⁴ is hydrogen or methyl; and R⁵ ishydrogen; X is O; Y is CR¹³R¹⁴; R¹³, R¹⁴ are hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-haloalkoxycarbonyl orCONR⁷R⁸; R⁷ is hydrogen or C₁-C₄-alkyl; and R⁸ is C₁-C₄-alkyl.
 2. The3-heterocyclyl-substituted benzoic acid compound of formula III definedin claim 1, wherein R¹⁹ is halogen, hydroxyl or C₁-C₆-alkoxy.
 3. A3-heterocyclyl-substituted benzoic acid compound of formula I

wherein: x is O; R¹ is C₁-C₂-alkyl, methoxy or methylsulfonyl; R² isnitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylthio,C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl or C₁-C₆-haloalkylsulfonyl; R³is hydrogen, halogen or C₁-C₆-alkyl; R⁴ is hydrogen or methyl; R⁵ ishydrogen; Y is CR¹³R¹⁴; R¹³, R¹⁴ are hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-haloalkoxycarbonyl orCONR⁷R⁸; R⁷ is hydrogen or C₁-C₄-alkyl; R⁸ is C₁-C₄-alkyl; R¹⁵ is apyrazole of the formula II which is linked in the 4-position

wherein R¹⁶ is C₁-C₆-alkyl; Z is H; and R¹⁸ is hydrogen or methyl.
 4. Acomposition comprising a herbicidally active amount of at least one3-heterocyclyl-substituted benzoyl compound of formula I or of theagriculturally useful salt of formula I defined in claim 3, andauxiliaries conventionally used for the formulation of crop protectionproducts.
 5. A process for the preparation of the composition defined inclaim 4, which comprises mixing a herbicidally active amount of at leastone 3-heterocyclyl-substituted benzoyl compound of the formula I or ofthe agriculturally useful salt of I and auxiliaries conventionally usedfor the formulation of crop protection products.
 6. A method ofcontrolling undesirable vegetation, which comprises allowing aherbicidally active amount of at least one 3-heterocyclyl-substitutedbenzoyl compound of the formula I or of the agriculturally useful saltof I defined in claim 3 to act on plants, their environment and/or onseeds.
 7. The 3-heterocyclyl-substituted benzoyl compound of the formulaI defined in claim 3, wherein R¹ is methyl, R² is methylsulfonyl, R³ ishydrogen, R¹⁶ is methyl and R¹⁸ is hydrogen. 8.4-[2-Methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-methyl-5-hydroxy-1H-pyrazole.9. The 3-heterocyclyl-substituted benzoyl compound of the formula Idefined in claim 3, wherein R¹ is methyl, R² is methylsulfonyl, R³ ishydrogen, R¹⁶ is ethyl and R¹⁸ is hydrogen.
 10. The3-heterocyclyl-substituted benzoyl compound of the formula I defined inclaim 3, wherein R¹ is methyl, R² is methyl-sulfonyl, R³ is hydrogen,R¹⁶ is methyl and R¹⁸ is methyl.
 11. The 3-heterocyclyl-substitutedbenzoyl compound of the formula I defined in claim 3, wherein R⁴ denoteshydrogen.
 12. The 3-heterocyclyl-substituted benzoyl compound of theformula I defined in claim 3, wherein R¹ is methyl.
 13. The3-heterocyclyl-substituted benzoyl compound of the formula I defined inclaim 11, wherein R¹ is methyl.
 14. The 3-heterocyclyl-substitutedbenzoyl compound of the formula I defined in claim 11, wherein R¹ ismethyl, R² is methylsulfonyl, R³ is hydrogen, R¹⁶ is ethyl and R¹⁸ ishydrogen.
 15. The 3-heterocyclyl-substituted benzoyl compound of theformula I defined in claim 11, wherein R¹ is methyl, R² ismethylsulfonyl, R³ is hydrogen, R¹⁶ is methyl and R¹⁸ is methyl.
 16. The3-heterocyclyl-substituted benzoic acid compound of the formula IIIdefined in claim 1, wherein R⁴ denotes hydrogen.
 17. The3-heterocyclyl-substituted benzoic acid compound of the formula IIIdefined in claim 1, wherein R¹ is methyl.
 18. The3-heterocyclyl-substituted benzoic acid compound of the formula IIIdefined in claim 16, wherein R¹ is methyl.
 19. The3-heterocyclyl-substituted benzoic acid compound of the formula IIIdefined in claim 2, wherein R⁴ denotes hydrogen.
 20. The3-heterocyclyl-substituted benzoic acid compound of the formula IIIdefined in claim 2, wherein R¹ is methyl.
 21. The3-heterocyclyl-substituted benzoic acid compound of the formula IIIdefined in claim 19, wherein R¹ is methyl.
 22. The3-heterocyclyl-substituted benzoic acid compound of the formula IIIdefined in claim 21, wherein R² is methylsulfonyl and R³ is hydrogen.23. The 3-heterocyclyl-substituted benzoyl compound of the formula Idefined in claim 3, wherein X is O; R¹ is C₁-C₂-alkyl; R² isC₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl; R³ is hydrogen; Y is CR¹³R¹⁴;and R¹³, R¹⁴ are hydrogen or C₁-C⁴-alkyl.
 24. The composition defined inclaim 4, comprising a herbicidally active amount of at least one3-heterocyclyl-substituted benzoyl compound of the formula I or of theagriculturally useful salt of I, wherein X is O; R¹ is C₁-C₂-alkyl; R²is C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl; R³ is hydrogen; Y is CR¹³R¹⁴;and R¹³, R¹⁴ are hydrogen or C₁-C₄-alkyl.
 25. The3-heterocyclyl-substituted benzoic acid compound of the formula IIIdefined in claim 1, wherein X is O; R¹ is C₁-C₂-alkyl; R² isC₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl; R³ is hydrogen; Y is CR¹³R¹⁴;and R¹³, R¹⁴ are hydrogen or C₁-C₄-alkyl.
 26. A compound represented byformula I

wherein R¹ is C₁-C₆-alkyl; R² is C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl;R³ is hydrogen; R⁴ and R⁵ are hydrogen or C₁-C₄-alkyl; X is CR¹⁰R¹¹,wherein R¹⁰ and R¹¹ are hydrogen or C₁-C₄-alkyl; Y is oxygen, and R¹⁵ isa pyrazole of formula II

which is linked in the 4-position, wherein R¹⁶ is C₁-C₆-alkyl; Z ishydrogen or SO₂R¹⁷, wherein R¹⁷ is phenyl or phenyl which is partiallyor fully halogenated and/or has attached to it one to three of thefollowing groups: C₁-C₄-alkyl and C₁-C₄-alkoxy; R¹⁸ is hydrogen orC₁-C₆-alkyl.
 27. A herbicide characterized by containing one or morecompounds represented by formula I

wherein R¹ is C₁-C₆-alkyl; R² is C₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl;R³ is hydrogen; R⁴ and R⁵ are hydrogen or C₁-C₄-alkyl; X is CR¹⁰R¹¹,wherein R¹⁰ and R¹¹ are hydrogen or C₁-C₄-alkyl; Y is oxygen, and R¹⁵ isa pyrazole of formula II

which is linked in the 4-position, wherein R¹⁶ is C₁-C₆-alkyl; Z ishydrogen or SO₂R¹⁷, wherein R¹⁷ is phenyl or phenyl which is partiallyor fully halogenated and/or has attached to it one to three of thefollowing groups: C₁-C₄-alkyl and C₁-C₄-alkoxy; R¹⁸ is hydrogen orC₁-C₆-alkyl, as active ingredients.
 28. A compound represented byformula III

wherein R¹⁹ is hydroxyl or C₁-C₆-alkoxy; R¹ is C₁-C₆-alkyl; R² isC₁-C₆-alkylthio or C₁-C₆-alkylsulfonyl; R³ is hydrogen; R⁴ and R⁵ arehydrogen or C₁-C₄-alkyl; X is CR¹⁰R¹¹, wherein R¹⁰ and R¹¹ are hydrogenor C₁-C₄-alkyl, and Y is oxygen.
 29. A process for the preparation ofthe 3-heterocyclyl-substituted benzoyl compound of the formula I definedin claim 28, which comprises acylating a pyrazole of the formula II

with an activated carboxylic acid IIIα or with a carboxylic acid IIIβ

where L¹ is a nucleophilically displaceable leaving group and subjectingthe acylation product to a rearrangement reaction to give the compoundI.